9,357 results match your criteria European Journal of Medicinal Chemistry [Journal]


A novel, potent, and orally bioavailable thiazole HCV NS5A inhibitor for the treatment of hepatitis C virus.

Eur J Med Chem 2019 Feb 6;167:245-268. Epub 2019 Feb 6.

Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli County 350, Taiwan, ROC. Electronic address:

A medicinal chemistry program based on the small-molecule HCV NS5A inhibitor daclatasvir has led to the discovery of dimeric phenylthiazole compound 8, a novel and potent HCV NS5A inhibitor. The subsequent SAR studies and optimization revealed that the cycloalkyl amide derivatives 27a-29a exhibited superior potency against GT1b with GT1b EC values at picomolar concentration. Interestingly, high diastereospecificity for HCV inhibition was observed in this class with the (1R,2S,1'R,2'S) diastereomer displaying the highest GT1b inhibitory activity. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.016DOI Listing
February 2019

Pyranocarbazole derivatives as potent anti-cancer agents triggering tubulin polymerization stabilization induced activation of caspase-dependent apoptosis and downregulation of Akt/mTOR in breast cancer cells.

Eur J Med Chem 2019 Feb 7;167:226-244. Epub 2019 Feb 7.

Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, Uttar Pradesh, India; Academy of Scientific and Innovative Research, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, Uttar Pradesh, India. Electronic address:

A series of new pyranocarbazole derivatives were synthesized via semi-synthetic modification of koenimbine (1a) and koenidine (1b) isolated from the leaves of Murraya koenigii. Among all, compound 3bg displayed significant anti-cancer activity against MDA-MB-231, DU145 and PC3 cell lines with the IC values of 3.8, 7. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.003DOI Listing
February 2019

Synthesis and evaluation of novel GSK-3β inhibitors as multifunctional agents against Alzheimer's disease.

Eur J Med Chem 2019 Feb 8;167:211-225. Epub 2019 Feb 8.

Institute of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan, 250012, PR China. Electronic address:

To target the multi-facets of Alzheimer's disease (AD), a series of novel GSK-3β inhibitors containing the 2,3-diaminopyridine moiety were designed and synthesized. The amide derivatives 5a-f showed moderate potency against GSK-3β with weak Cu, Zn and Al chelating ability. The imine derivatives 9a, 9b and 9e were potent GSK-3β inhibitors and selective Cuand Al chelators. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.001DOI Listing
February 2019

2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as potent staphylococcal biofilm inhibitors.

Eur J Med Chem 2019 Feb 10;167:200-210. Epub 2019 Feb 10.

Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche (STEBICEF), Università degli Studi di Palermo, Via Archirafi 32, 90123, Palermo, Italy. Electronic address:

A class of 36 new 2-(6-phenylimidazo[2,-1-b][1,3,4]thiadiazol-2-yl)-1H-indoles was efficiently synthesized and evaluated for their anti-biofilm properties against the Gram-positive bacterial reference strains Staphylococcus aureus ATCC 25923, S. aureus ATCC 6538 and Staphylococcus epidermidis ATCC 12228, and the Gram-negative strains Pseudomonas aeruginosa ATCC 15442 and Escherichia coli ATCC 25922. Many of these new compounds, were able to inhibit biofilm formation of the tested staphylococcal strains showing BIC lower than 10 μg/ml. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.007DOI Listing
February 2019
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Dissymmetric pyridyl-substituted 3,5-bis(arylidene)-4-piperidones as anti-hepatoma agents by inhibiting NF-κB pathway activation.

Eur J Med Chem 2019 Feb 7;167:187-199. Epub 2019 Feb 7.

School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical Evaluation of State Administration of Traditional Chinese Medicine of China, Binzhou Medical University, Yantai, 264003, PR China. Electronic address:

To get new anti-hepatoma agents with anti-inflammatory activity and hypotoxicity, a series of dissymmetric pyridyl-substituted 3,5-bis(arylidene)-4-piperidones (BAPs, 25-82) were designed and synthesized. Many of them exhibited potential anti-hepatoma properties against human hepatocellular carcinoma cell lines (HepG2, QGY-7703, SMMC-7721) and hypotoxicity for human normal heptical cell line (HHL-5, LO2), and prominently inhibited lipopolysaccharides (LPS) induced IL-6, TNF-α secretion to exert its anti-inflammatory effect. Combining the data of cytotoxicity, cytocompatibility and anti-inflammatory activity, 3-pyridyl and -CF substituted 67 may be the potential anti-hepatoma agent. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.020DOI Listing
February 2019

Tackling neuroinflammation and cholinergic deficit in Alzheimer's disease: Multi-target inhibitors of cholinesterases, cyclooxygenase-2 and 15-lipoxygenase.

Eur J Med Chem 2019 Feb 8;167:161-186. Epub 2019 Feb 8.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria, 21521, Egypt. Electronic address:

Neuroinflammation and cholinergic deficit are key detrimental processes involved in Alzheimer's disease. Hence, in the search for novel and effective treatment strategies, the multi-target-directed ligand paradigm was applied to the rational design of two series of new hybrids endowed with anti-inflammatory and anticholinesterase activity via triple targeting properties, namely able to simultaneously hit cholinesterases, cyclooxygenase-2 (COX-2) and 15-lipoxygenase (15-LOX) enzymes. Among the synthesized compounds, triazoles 5b and 5d, and thiosemicarbazide hybrid 6e emerged as promising new hits, being able to effectively inhibit human butyrylcholinesterase (hBChE), COX-2 and 15-LOX enzymes with a higher inhibitory potency than the reference inhibitors tacrine (for hBChE inhibition), celecoxib (for COX-2 inhibition) and both NDGA and Zileuton (for 15-LOX inhibition). Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.012DOI Listing
February 2019

Discovery of a new class of MTH1 inhibitor by X-ray crystallographic screening.

Eur J Med Chem 2019 Feb 7;167:153-160. Epub 2019 Feb 7.

Faculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama, 930-0914, Japan; Graduate School of Innovative Life Science, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan.

MutT homologue 1 (MTH1) protects the nucleotide pool from oxidative stress by hydrolyzing oxidized nucleoside triphosphates and prevents their incorporation into DNA. Cancer cells are dependent on the MTH1 activity for survival due to the high-level of reactive oxygen species in cancer cells; therefore, MTH1 is considered to be a novel target for treatment of various cancers. Here, we show by X-ray crystallographic screening using an in-house cocktail library that α-mangostin, a natural xanthone from mangosteen pericarp, binds to the active site of MTH1. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.011DOI Listing
February 2019

Repurposing nitrocatechols: 5-Nitro-α-cyanocarboxamide derivatives of caffeic acid and caffeic acid phenethyl ester effectively inhibit aggregation of tau-derived hexapeptide AcPHF6.

Eur J Med Chem 2019 Feb 4;167:146-152. Epub 2019 Feb 4.

CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre s/n, 4169-007, Porto, Portugal. Electronic address:

Polyphenols like caffeic acid and its phenethyl ester have been associated with potent anti-aggregating activity. Accordingly, we screened a library of polyphenols and synthetic derivatives thereof for their capacity to inhibit tau-aggregation using a thioflavin T-based fluorescence method. Our results show that the nitrocatechol scaffold is required for a significant anti-aggregating activity, which is enhanced by introducing bulky substituents at the side chain. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.006DOI Listing
February 2019

Synthesis and evaluation of tetrahydroisoquinoline-benzimidazole hybrids as multifunctional agents for the treatment of Alzheimer's disease.

Eur J Med Chem 2019 Feb 4;167:133-145. Epub 2019 Feb 4.

Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China. Electronic address:

A novel series of tetrahydroisoquinoline-benzimidazole hybrids have been designed and synthesized as multifunctional agents against Alzheimer's disease (AD). These compounds were evaluated for their inhibition of neuroinflammation and human β-secretase (hBACE1), and neuroprotective activity. Among them, compound BD3 possessed significant anti-neuroinflammatory activity (IC = 5. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.008DOI Listing
February 2019

Synthesis, docking and antibacterial studies of more potent amine and hydrazone rifamycin congeners than rifampicin.

Eur J Med Chem 2019 Feb 4;167:96-104. Epub 2019 Feb 4.

Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614, Poznan, Poland. Electronic address:

New rifamycin congeners (1-33) with incorporated amine and hydrazone substituents leading to lipophilic and/or basic nature and altered rigidity of modified C(3) arm were synthesized and structurally characterized in detail. NMR spectroscopic studies at different temperatures indicate two types of structures of rifamycin congeners that are realized in solution: zwitterionic and non-ionic forms in dependence of the basicity of modified C(3) arm. The presence of rifamycin congeners in these two possible forms has a significant impact on the physico-chemical parameters such as lipophilicity (clogP) and water solubility and different binding mode of the C(3) arm of antibiotic at RNAP binding pocket (molecular target) leading to different antibacterial potency. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.009DOI Listing
February 2019

Clinical candidates modulating protein-protein interactions: The fragment-based experience.

Eur J Med Chem 2019 Feb 5;167:76-95. Epub 2019 Feb 5.

Department of Biomedical Engineering and Institute for Complex Molecular Systems, Technische Universiteit Eindhoven, Den Dolech 2, 5612, AZ, Eindhoven, the Netherlands; Department of Chemistry, University of Duisburg-Essen, Universitätsstraße 7, 45117, Essen, Germany. Electronic address:

Protein-protein interactions (PPIs) cover a very wide range of biological functions and consequently have become one of the favourite targets for new therapeutic strategies. PPIs are strongly characterised by an intricate and dynamic network of surface interactions occurring between two or more proteins. Because of the complexity of these interactions, many strategies have been applied with the aim to find selective modulators for a specific protein-protein complex. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.084DOI Listing
February 2019

First-in-class allosteric inhibitors of bacterial IMPDHs.

Eur J Med Chem 2019 Feb 2;167:124-132. Epub 2019 Feb 2.

Institut Pasteur, Unité de Chimie et Biocatalyse, Département de Biologie Structurale et Chimie, CNRS UMR3523, 28 rue du Dr Roux, F-75015, Paris, France. Electronic address:

Inosine-5'-monophosphate dehydrogenase (IMPDH) is an essential enzyme in many bacterial pathogens and is considered as a potential drug target for the development of new antibacterial agents. Our recent work has revealed the crucial role of one of the two structural domains (i.e. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.064DOI Listing
February 2019

Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation.

Eur J Med Chem 2019 Feb 4;167:105-123. Epub 2019 Feb 4.

Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, PR China. Electronic address:

A series of aminothiazolyl norfloxacin analogues as a new type of potential antimicrobial agents were synthesized and screened for their antimicrobial activities. Most of the prepared compounds exhibited excellent inhibitory efficiencies. Especially, norfloxacin analogue II-c displayed superior antimicrobial activities against K. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.072DOI Listing
February 2019

Pharmacological urate-lowering approaches in chronic kidney disease.

Eur J Med Chem 2019 Jan 23;166:186-196. Epub 2019 Jan 23.

Kidney Research Laboratory, Division of Nephrology and National Clinical Research Center for Geriatrics, West China Hospital of Sichuan University, Chengdu, 610041, China. Electronic address:

Chronic kidney disease (CKD) has become a global public health issue and uric acid (UA) remains a major risk factor of CKD. As the main organ for the elimination of UA, kidney owned a group of urate transporters in tubular epithelium. Kidney disease hampered the UA excretion, and the accumulation of serum UA in return harmed the renal function. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.043DOI Listing
January 2019

Identification of an indol-based multi-target kinase inhibitor through phenotype screening and target fishing using inverse virtual screening approach.

Eur J Med Chem 2019 Feb 6;167:61-75. Epub 2019 Feb 6.

Department of Pharmacy, University of Salerno, Via G. Paolo II, 84084, Fisciano, SA, Italy. Electronic address:

A series of 1,3,5-substituted indole derivatives was prepared to explore the anti-proliferative activity against a panel of human tumour cell lines. A 5-carboxamide derivative (27) emerged as the most potent compound of this series, inhibiting the HeLa cell growth at sub-micromolar concentrations. Target fishing of 27 using a combination of inverse virtual screening (IVS) approach and ligand-based shape similarity study identified the top-ranked targets for 27 as belonging to kinome. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193008
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http://dx.doi.org/10.1016/j.ejmech.2019.01.066DOI Listing
February 2019
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Discovery of deshydroxy bicalutamide derivatives as androgen receptor antagonists.

Eur J Med Chem 2019 Feb 2;167:49-60. Epub 2019 Feb 2.

School of Pharmacy & Pharmaceutical Sciences, Cardiff University, King Edward VII Avenue, Cardiff, CF10 3NB, Wales, UK.

Deshydroxy propioanilides were synthesised by Michael addition reaction between substituted thiophenols onto four different phenylacrylamide derivatives to give twenty-three novel deshydroxy bicalutamide derivatives lacking the central hydroxyl group. The antiproliferative activities of these compounds were evaluated against human prostate cancer cell lines and thirteen compounds showed better inhibitory activities (IC = 2.67-13. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.054DOI Listing
February 2019

Discovery of N-indanyl benzamides as potent RORγt inverse agonists.

Eur J Med Chem 2019 Feb 4;167:37-48. Epub 2019 Feb 4.

Department of Medicinal Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China. Electronic address:

The retinoic acid receptor-related orphan receptor-gamma-t (RORγt) is a promising therapeutic target for treatment of Th17 cell-mediated autoimmune diseases. Based on a scaffold hopping/conformational restriction strategy, a series of N-indanyl benzamides as novel RORγt inverse agonists was discovered. Exploration of structure-activity relationship on the piperazine ring, benzoyl moiety and cyclopentyl moiety of N-indanyl benzamides 2a and 2d led to identification of potent RORγt inverse agonists. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.082DOI Listing
February 2019

Toward the discovery and development of effective modulators of α-synuclein amyloid aggregation.

Eur J Med Chem 2019 Jan 28;167:10-36. Epub 2019 Jan 28.

Dipartimento di Scienze Chimiche, Università degli Studi di Catania, viale A. Doria 6, 95125, Catania, Italy. Electronic address:

A host of human diseases, including Parkinson's disease and Dementia with Lewy bodies, are suspected to be directly linked to protein aggregation. Amyloid protein aggregates and oligomeric intermediates of α-synuclein are observed in synucleinopathies and considered to be mediators of cellular toxicity. Hence, α-synuclein has seen as one of the leading and most compelling targets and is receiving a great deal of attention from researchers. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.045DOI Listing
January 2019
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Pyridine and nitro-phenyl linked 1,3,4-thiadiazoles as MDR-TB inhibitors.

Eur J Med Chem 2019 Feb 4;167:1-9. Epub 2019 Feb 4.

Department of Pharmaceutical Chemistry, R. C. Patel Institute of Pharmaceutical Education and Research, Shirpur, India.

In the present study, a series of substituted 1,3,4-thiadiazole derivatives 4(a-o), 5(a-m) and 6(a-j) were synthesized and characterized by IR, H NMR, C NMR and mass spectroscopic technique. The synthesized compounds were evaluated for their in vitro anti-mycobacterial activity against the Mycobacterium tuberculosis H37Rv and resistance MDR-TB strain. Among the compounds tested N-(5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)furan-2-carboxamide (4h) showed significant inhibitory activity with MIC of 9. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193009
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http://dx.doi.org/10.1016/j.ejmech.2019.01.073DOI Listing
February 2019
2 Reads

Role of PPAR receptor in different diseases and their ligands: Physiological importance and clinical implications.

Eur J Med Chem 2019 Feb 1;166:502-513. Epub 2019 Feb 1.

Research Institute of Pharmaceutical Sciences, Faculty of Pharmacy, University of Karachi, Karachi, 75270, Pakistan.

The peroxisome proliferator-activated receptors (PPAR-α, PPAR-β/δ, and PPAR-γ) are members of the nuclear receptor super-family, acting as ligand-inducible transcription factors and play crucial roles in glucose and lipid metabolism. These are a well-known receptor for diabetic therapy, not only influence the cardiovascular systems but are also expressed in many human solid tumors. For atherosclerosis, inflammation, and hypertension, the PPARs are considered as important therapeutic targets. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.067DOI Listing
February 2019

Design and synthesis of aminothiazole based Hepatitis B Virus (HBV) capsid inhibitors.

Eur J Med Chem 2019 Feb 5;166:480-501. Epub 2019 Feb 5.

Institute of Human Virology, Sun Yat-sen University, Guangzhou, Guangdong, 510080, China; Key Laboratory of Tropical Disease Control of Ministry of Education, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, Guangdong, 510080, China; Guangdong Engineering Research Center for Antimicrobial Agent and Immunotechnology, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, Guangdong, 510080, China. Electronic address:

The capsid assembly is an essential step for Hepatitis B Virus (HBV) life cycle and is an important target for anti-HBV drug development. In this report, we identified a hit compound with aminothiazole structure by the high throughput screening (HTS) which inhibited the interaction of HBV capsid protein within the cells. The structure hopping and SAR studies of the hit compound afforded compound 79 with potent anti-HBV replication activity and good basic drug-like properties. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.059DOI Listing
February 2019
1 Read

Excellent antitumor and antimetastatic activities based on novel coumarin/pyrazole oxime hybrids.

Eur J Med Chem 2019 Jan 30;166:470-479. Epub 2019 Jan 30.

College of Chemistry and Chemical Engineering, Nantong University, Nantong, 226019, People's Republic of China; School of Pharmacy, Nantong University, Nantong, 226001, People's Republic of China; Jiangsu Province Key Laboratory for Inflammation and Molecular Drug Target, Nantong University, Nantong, 226001, People's Republic of China. Electronic address:

A series of hybrids 10a-v based on coumarin/pyrazole oxime have been synthesized, and exhibit good to excellent antitumor activities. Compound 10n has shown remarkable anticancer effect on SMMC-7721 cells (IC = 2.08 μM), which is considerably lower than 5-FU (IC = 37. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.070DOI Listing
January 2019

Synthesis and structure-activity relationship studies of parthenolide derivatives as potential anti-triple negative breast cancer agents.

Eur J Med Chem 2019 Feb 1;166:445-469. Epub 2019 Feb 1.

State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Haihe Education Park, 38 Tongyan Road, Tianjin, 300353, People's Republic of China. Electronic address:

Triple-negative breast cancer (TNBC) is the most aggressive cancers with a high recurrence rate and rapidly acquired drug resistance among various breast cancer subtypes. There is no specific drug for treatment of TNBC. Discovery of therapeutic agents with unique modes of actions is urgently needed. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.058DOI Listing
February 2019

Experience-based discovery (EBD) of aryl hydrazines as new scaffolds for the development of LSD1/KDM1A inhibitors.

Eur J Med Chem 2019 Feb 2;166:432-444. Epub 2019 Feb 2.

School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, China; Key Laboratory of Advanced Drug Preparation Technologies (Ministry of Education), Zhengzhou University, Zhengzhou 450001, China; Co-Innovation Center of Henan Province for New Drug R & D and Preclinical Safety, Zhengzhou University, Zhengzhou 450001, China. Electronic address:

Phenelzine was first employed to design new aryl hydrazine-based LSD1 inhibitors based on the experience-based discovery (EBD) strategy. Among these compounds, D8 potently inhibited LSD1 (IC = 882.30 nM) in a reversible manner. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.075DOI Listing
February 2019
1 Read

Aurone: A biologically attractive scaffold as anticancer agent.

Eur J Med Chem 2019 Feb 1;166:417-431. Epub 2019 Feb 1.

College of Applied Medical Sciences, King Khalid University, Abha, 62529, Saudi Arabia.

Aurones are very simple, promising anticancer lead molecules containing three rings (A, B and C). A very slight structural variation in the aurones elicits diverse affinity and specificity towards different molecular targets. The present review discusses the design, discovery and development of natural and synthetic aurones as small molecule anticancer agents. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.078DOI Listing
February 2019
3.447 Impact Factor

An overview of grayanane diterpenoids and their biological activities from the Ericaceae family in the last seven years.

Eur J Med Chem 2019 Feb 1;166:400-416. Epub 2019 Feb 1.

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A & F University, Yangling, 712100, Shaanxi, People's Republic of China. Electronic address:

Grayanane diterpenoids, possessing a unique 5/7/6/5 tetracyclic system, exist exclusively in plants of the Ericaceae family. Owing to their various skeletons, complex structures, and diverse bioactivities, grayanoids have been the topic of research in many phytochemical and pharmacological laboratories, offering opportunities for the development of new drugs with analgesic, anti-inflammatory, and protein tyrosine phosphatase 1B (PTP1B) properties. Recently, a number of new grayanane diterpenoids with unprecedented carbon skeletons have been obtained from plants of the Ericaceae family, and they exhibit diverse biological properties, such as agalgesic, antinociceptive, anticancer, antiviral, antifeedant, insecticidal, toxicity, and PTP1B. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.079DOI Listing
February 2019

Pharmacophore-based design of novel 3-hydroxypyrimidine-2,4-dione subtypes as inhibitors of HIV reverse transcriptase-associated RNase H: Tolerance of a nonflexible linker.

Eur J Med Chem 2019 Feb 2;166:390-399. Epub 2019 Feb 2.

Center for Drug Design, College of Pharmacy, University of Minnesota, Minneapolis, MN, 55455, USA. Electronic address:

The pharmacophore of active site inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H typically entails a flexible linker connecting the chelating core and the hydrophobic aromatics. We report herein that novel 3-hydroxypyrimidine-2,4-dione (HPD) subtypes with a nonflexible C-6 carbonyl linkage exhibited potent and selective biochemical inhibitory profiles with strong RNase H inhibition at low nM, weak to moderate integrase strand transfer (INST) inhibition at low μM, and no to marginal RT polymerase (pol) inhibition up to 10 μM. A few analogues also demonstrated significant antiviral activity without cytotoxicity. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193010
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http://dx.doi.org/10.1016/j.ejmech.2019.01.081DOI Listing
February 2019
2 Reads

Tacrines for Alzheimer's disease therapy. III. The PyridoTacrines.

Eur J Med Chem 2019 Feb 4;166:381-389. Epub 2019 Feb 4.

Laboratory of Medicinal Chemistry (IQOG, CSIC), 3, Juan de la Cierva, 28006, Madrid, Spain. Electronic address:

Tacrine was the first drug approved for the treatment of Alzheimer's disease (AD) in 1993, which was withdrawn in 2013 due to its hepatotoxicity. However, new, non-hepatotoxic tacrine derivatives have been constantly searched for. In this context, since 1997, we have prepared a number of diversely functionalized tacrines by changing the benzene ring present in tacrine to five- or six-membered aromatic ring cores that could present anticholinesterasic activity and additional pharmacological properties. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.02.005DOI Listing
February 2019
1 Read

Histone deacetylase 3 inhibitors in learning and memory processes with special emphasis on benzamides.

Eur J Med Chem 2019 Jan 31;166:369-380. Epub 2019 Jan 31.

Department of Pharmacy, BITS-Pilani, Hyderabad Campus, Shamirpet, Hyderabad, 500078, India. Electronic address:

Among numerous essential processes, memory and learning are important work of the brain. Epigenetic manipulations through histone acetyltransferases (HATs) and histone deacetylases (HDACs) have been implicated in memory function by modulating memory storage-related gene expression. Among these HDACs, HDAC3 is found to be important in the long-term memory process. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.077DOI Listing
January 2019

Histone methyl transferases: A class of epigenetic opportunities to counter uncontrolled cell proliferation.

Eur J Med Chem 2019 Feb 1;166:351-368. Epub 2019 Feb 1.

Department of Pharmaceutical Sciences and Drug Research, Punjabi University, Patiala, Punjab, 147002, India. Electronic address:

With each newly disclosed resistance mechanism, management of cancer with previously established targets have become a "failure" oriented approach. Molecular targets such as kinases did initially provide a ray of hope against cancer but with decades of struggle between novel therapeutic agents and more sophisticated resistance mechanisms, they seem to have saturated as anti-cancer targets. Now, with more exhaustive molecular recognition techniques and approaches, epigenetic targets have accessed the centre stage as anti-cancer targets. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193008
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http://dx.doi.org/10.1016/j.ejmech.2019.01.069DOI Listing
February 2019
1 Read

Synthesis of 7-benzylguanosine cap-analogue conjugates for eIF4E targeted degradation.

Eur J Med Chem 2019 Jan 31;166:339-350. Epub 2019 Jan 31.

Department of Medicinal Chemistry, College of Pharmacy, University of Michigan, 1600 Huron Parkway, Ann Arbor, MI, 48109, USA. Electronic address:

Eukaryotic translation initiation factor 4E (eIF4E) is a key player in the initiation of cap-dependent translation through recognition of the mGpppX cap at the 5' terminus of coding mRNAs. As eIF4E overexpression has been observed in a number of human diseases, most notably cancer, targeting this oncogenic translation initiation factor has emerged as a promising strategy for the development of novel anti-cancer therapeutics. Toward this end, in the present study, we have rationally designed a series of BnGxP-based PROTACs for the targeted degradation of eIF4E. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.080DOI Listing
January 2019
1 Read

Synthesis and structure-activity relationship studies of water-soluble β-cyclodextrin-glycyrrhetinic acid conjugates as potential anti-influenza virus agents.

Eur J Med Chem 2019 Jan 30;166:328-338. Epub 2019 Jan 30.

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China. Electronic address:

Glycyrrhetinic acid (GA) is a major constituent of the herb Glycyrrhiza glabra, and many of its derivatives demonstrate a broad spectrum of antiviral activities. In the current study, 18 water-soluble β-cyclodextrin (CD)-GA conjugates, in which GA was covalently coupled to the primary face of β-CD using 1,2,3-triazole moiety along with varying lengths of linker, were synthesized via copper-catalyzed azide-alkyl cycloaddition reaction. Benefited from the attached β-CD moiety, all these conjugates showed lower hydrophobicity (AlogP) compared with their parent compound GA. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.074DOI Listing
January 2019

Quinolone antibiotic derivatives as new selective Axl kinase inhibitors.

Eur J Med Chem 2019 Jan 30;166:318-327. Epub 2019 Jan 30.

International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development, Ministry of Education (MOE) of People's Republic of China and Guangzhou City Key Laboratory of Precision Chemical Drug Development, School of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou, 510632, China. Electronic address:

Axl is a new promising molecular target for antineoplastic therapies. A series of quinolone antibiotic derivatives were designed and synthesized as new selective Axl inhibitors. One of the most promising compound 8i bound tightly to Axl with a K value of 1. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.065DOI Listing
January 2019
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New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis.

Eur J Med Chem 2019 Jan 26;166:304-317. Epub 2019 Jan 26.

Université Clermont Auvergne, CNRS, SIGMA Clermont, ICCF, F-63000, Clermont-Ferrand, France. Electronic address:

Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.052DOI Listing
January 2019
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2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma.

Eur J Med Chem 2019 Jan 22;166:291-303. Epub 2019 Jan 22.

Molecular Signaling Lab, Faculty of Medicine and Health Technology, Tampere University and BioMediTech, P.O. Box 553, 33101, Tampere, Finland. Electronic address:

Nerve growth factor receptor (NGFR), a member of kinase protein, is emerging as an important target for Glioblastoma (GBM) treatment. Overexpression of NGFR is observed in many metastatic cancers including GBM, promoting tumor migration and invasion. Hydrazones have been reported to effectively interact with receptor tyrosine kinases (RTKs). Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.021DOI Listing
January 2019
2 Reads

Structure-based drug design, synthesis, In vitro, and In vivo biological evaluation of indole-based biomimetic analogs targeting estrogen receptor-α inhibition.

Eur J Med Chem 2019 Jan 30;166:281-290. Epub 2019 Jan 30.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The British University in Egypt, El-Sherouk, Cairo, Egypt; Center of Drug Research and Development (CDRD), The British University in Egypt, El-Sherouk, Cairo, Egypt; Department of Internal Medicine, Division of Cardiology, University of Texas Southwestern Medical Center, Dallas, TX, USA. Electronic address:

Offering novel scaffolds targeting estrogen receptor creates huge necessity to overcome the evolving resistance developed by tumors. Structure-based drug design coupled with ring opening strategy of the steroids skeleton revealed the potential of indole-based analogs to be synthesized targeting the ligand binding domain of estrogen receptor-α. In vitro studies revealed the potential of the total sub-classes of the synthesized analogs to show anti-proliferative activity against estrogen receptor-dependent cancer cell lines at IC ranging from 28. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.068DOI Listing
January 2019
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Synthesis of 5-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzylidene)thiazolidine-2,4-dione as promising DNA and serum albumin-binding agents and evaluation of antitumor activity.

Eur J Med Chem 2019 Jan 26;166:267-280. Epub 2019 Jan 26.

School of Chemistry and Biochemistry, Thapar Institute of Engineering & Technology, Patiala 147 001, India. Electronic address:

A series of phenanthro[9,10-d]imidazole/oxazole and acenaphtho[1,2-d]imidazole with different aryl groups at C2-position has been synthesized. These compounds were in vitro evaluated for antitumor activity against a panel of 60 human cancer cell lines. Compound 8 exhibits higher cytotoxicity towards leukemia, colon, melanoma, renal, and breast cancer cell lines than the other evaluated cell panels and low toxicity against normal cell line Hek293. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.053DOI Listing
January 2019
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Development of bioactive gemcitabine-D-Lys-GnRH prodrugs with linker-controllable drug release rate and enhanced biopharmaceutical profile.

Eur J Med Chem 2019 Jan 18;166:256-266. Epub 2019 Jan 18.

Department of Chemistry, Section of Organic Chemistry and Biochemistry, Laboratory of Chemical Biology, University of Ioannina, Ioannina, GR-45110, Greece. Electronic address:

Peptide-drug conjugates have emerged as a potent approach to enhance the targeting and pharmacokinetic profiles of drugs. However, the impact of the linker unit has not been explored/exploited in depth. Gemcitabine (dFdC) is an anticancer agent used against a variety of solid tumours. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.041DOI Listing
January 2019
2 Reads
3.447 Impact Factor

Synthesis of new derivatives of boehmeriasin A and their biological evaluation in liver cancer.

Eur J Med Chem 2019 Jan 24;166:243-255. Epub 2019 Jan 24.

School of Chemistry, University College Dublin, Science Centre South, Belfield, Dublin 4, Ireland. Electronic address:

Two series of boehmeriasin A analogs have been synthesized in short and high yielding processes providing derivatives differing either in the alkaloid's pentacyclic scaffold or its peripheral substitution pattern. These series have enabled, for the first time, comparative studies into key biological properties revealing a new lead compound with exceptionally high activity against liver cancer cell lines in the picomolar range for both well (Huh7, Hep3B and HepG2) and poorly (Mahlavu, FOCUS and SNU475) differentiated cells. The cell death was characterized as apoptosis by cytochrome-C release, PARP protein cleavage and SubG1 cell cycle arrest. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193006
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http://dx.doi.org/10.1016/j.ejmech.2019.01.056DOI Listing
January 2019
5 Reads

Rational drug design for androgen receptor and glucocorticoids receptor dual antagonist.

Eur J Med Chem 2019 Jan 26;166:232-242. Epub 2019 Jan 26.

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004, PR China. Electronic address:

Prostate cancer (PCa) is the most frequently diagnosed male malignant tumor and remains the second leading cause of male cancer mortality in the western countries. The second-generation antiandrogen enzalutamide (ENZa) can prolong survival time for patients with mCRPC. However, the overexpression of glucocorticoids receptor (GR) in mCRPC cells causes the resistance of antiandrogen and leads to the failure of androgen receptor (AR) targeting therapy. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.036DOI Listing
January 2019

Design, synthesis and anti-bacterial studies of piperazine derivatives against drug resistant bacteria.

Eur J Med Chem 2019 Jan 27;166:224-231. Epub 2019 Jan 27.

Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, Abbottabad, 22060, Pakistan. Electronic address:

In current research, five series of mono- and di-substituted piperazine derivatives have been synthesized. For di-substituted derivatives, ciprofloxacin was selected and hybrids were synthesized via substitution at piperazinyl-N. In vitro antibacterial studies of all synthesized compound were carried out against American Type Culture Collection (ATCC) strains; E. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.062DOI Listing
January 2019

Triazole derivatives and their antiplasmodial and antimalarial activities.

Eur J Med Chem 2019 Jan 25;166:206-223. Epub 2019 Jan 25.

Zhejiang Provincial Engineering Technology Research Center of Marine Biomedical Products, School of Food and Pharmacy, Zhejiang Ocean University, Zhoushan, Zhejiang 316022, PR China. Electronic address:

Malaria, caused by protozoan parasites of the genus Plasmodium especially by the most prevalent parasite Plasmodium falciparum, represents one of the most devastating and common infectious disease globally. Nearly half of the world population is under the risk of being infected, and more than 200 million new clinical cases with around half a million deaths occur annually. Drug therapy is the mainstay of antimalarial therapy, yet current drugs are threatened by the development of resistance, so it's imperative to develop new antimalarials with great potency against both drug-susceptible and drug-resistant malaria. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.047DOI Listing
January 2019
1 Read

Repurposing ibuprofen to control Staphylococcus aureus biofilms.

Eur J Med Chem 2019 Jan 24;166:197-205. Epub 2019 Jan 24.

LEPABE - Department of Chemical Engineering, Faculty of Engineering, University of Porto, Rua Dr. Roberto Frias, s/n, Porto, 4200-465, Portugal. Electronic address:

Drug repurposing arises as an interesting alternative to overcome the limited efficacy of current available antibiotics by reducing time, cost and risk associated with drug innovation. In this study, the activity of ibuprofen, a non-steroidal anti-inflammatory drug (NSAID), was evaluated on the control of pre-established adhered cells (2 h) and 24 h old biofilms of Staphylococcus aureus. Bacterial adhesion was performed by S. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.046DOI Listing
January 2019
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Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors.

Eur J Med Chem 2019 Jan 25;166:178-185. Epub 2019 Jan 25.

State Key Laboratory of Microbial Technology, Shandong University, Qingdao, China. Electronic address:

Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193007
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http://dx.doi.org/10.1016/j.ejmech.2019.01.057DOI Listing
January 2019
1 Read
3.447 Impact Factor

Optimizing TRPM4 inhibitors in the MHFP6 chemical space.

Eur J Med Chem 2019 Jan 24;166:167-177. Epub 2019 Jan 24.

Department of Chemistry and Biochemistry, National Center for Competence in Research NCCR TransCure, University of Berne, Freiestrasse 3, 3012, Bern, Switzerland. Electronic address:

We recently reported 4-chloro-2-(2-chlorophenoxy)acetamido)benzoic acid (CBA) as the first potent inhibitor of TRPM4, a cation channel implicated in cardiac diseases and prostate cancer. Herein we report a structure-activity relationship (SAR) study of CBA resulting in two new potent analogs. To design and interpret our SAR we used interactive color-coded 3D-maps representing similarities between compounds calculated with MHFP6 (MinHash fingerprint up to six bonds), a new molecular fingerprint outperforming other fingerprints in benchmarking virtual screening studies. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.048DOI Listing
January 2019
2 Reads

1,2,4-Triazolo[1,5-a]pyrimidines in drug design.

Eur J Med Chem 2019 Mar 14;165:332-346. Epub 2019 Jan 14.

Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA. Electronic address:

The 1,2,4-triazolo[1,5-a]pyrimidine (TP) heterocycle, in spite of its relatively simple structure, has proved to be remarkably versatile as evidenced by its use in many different applications reported over the years in different areas of drug design. For example, as the ring system of TPs is isoelectronic with that of purines, this heterocycle has been proposed as a possible surrogate of the purine ring. However, depending on the choice of substituents, the TP ring has also been described as a potentially viable bio-isostere of the carboxylic acid functional group and of the N-acetyl fragment of ε-N-acetylated lysine. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.027DOI Listing
March 2019
1 Read

Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity.

Eur J Med Chem 2019 Jan 10;166:159-166. Epub 2019 Jan 10.

Natural Products Research Laboratories, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC, 27599, USA; Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 404, Taiwan. Electronic address:

In this study, 12 known cycloartane triterpenoids (1-12) with four different skeletons isolated from the roots of Souliea vaginata were screened for the first time for in vitro anti-HIV activity using AZT as a standard. Among the compounds, beesioside I (1) showed the highest potency against HIV-1 with an EC value of 2.32 μM (CC > 40 μM). Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193003
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http://dx.doi.org/10.1016/j.ejmech.2019.01.020DOI Listing
January 2019
7 Reads

Synthesis of novel pyrido[1,2-c]pyrimidine derivatives with rigidized tryptamine moiety as potential SSRI and 5-HT receptor ligands.

Eur J Med Chem 2019 Jan 22;166:144-158. Epub 2019 Jan 22.

Department of Drug Technology and Pharmaceutical Biotechnology, Faculty of Pharmacy, Medical University of Warsaw, 1, Banacha Street, 02-097 Warsaw, Poland.

The study enabled obtaining a number of new derivatives of 4-aryl-pyrido[1,2-c]pyrimidine 9.1-9.27 having conformationally restricted tryptamine moiety. Read More

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https://linkinghub.elsevier.com/retrieve/pii/S02235234193004
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http://dx.doi.org/10.1016/j.ejmech.2019.01.031DOI Listing
January 2019
3 Reads

Chikungunya virus inhibition by synthetic coumarin-guanosine conjugates.

Eur J Med Chem 2019 Jan 21;166:136-143. Epub 2019 Jan 21.

Department of Chemistry, National Tsing Hua University, Hsinchu, 300, Taiwan; Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu, 300, Taiwan; Department of Chemistry, National Central University, Jhongli City, Taoyuan, 320, Taiwan. Electronic address:

Since its discovery in Tanganyika, Africa in 1952, chikungunya virus (CHIKV) outbreaks have occurred in Africa, Asia, Europe, and America. Till now chikungunya fever has spread in nearly 40 countries. Because of lack of effective vaccines and antiviral drugs to intervene this disease, 21 new conjugated compounds were designed and synthesized by coupling of 6,8-dithioguanosine at its C-6 position with 3-(chloromethyl)coumarins bearing an F, Cl, Br, Me, or -OMe substituent through the -SCH- joint. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.037DOI Listing
January 2019
4 Reads

Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis.

Eur J Med Chem 2019 Jan 23;166:125-135. Epub 2019 Jan 23.

Saint Petersburg State University, Saint Petersburg, 199034, Russian Federation; Saint Petersburg Research Institute of Phthisiopulmonology, 2-4 Ligovsky Prospekt, Saint Petersburg, 191036, Russian Federation.

A selectively antimycobacterial compound belonging to the nitrofuran class of antimicrobials has been developed via conjugation of the nitrofuran moiety to a series of spirocyclic piperidines through an amide linkage. It proved to have comparable activity against drug-sensitive (H37Rv) strain as well as multidrug-resistant, patient-derived strains of Mycobacterium tuberculosis. The compound is druglike, showed no appreciable cytotoxicity toward human retinal pigment epithelial cell line ARPE-19 in concentrations up to 100 μM and displayed low toxicity when evaluated in mice. Read More

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http://dx.doi.org/10.1016/j.ejmech.2019.01.050DOI Listing
January 2019
1 Read