2,764 results match your criteria Bioorganic chemistry[Journal]


Prenylated chromones and flavonoids from Artocarpus heterophyllus with their potential antiproliferative and anti-inflammatory activities.

Bioorg Chem 2020 Jun 20;101:104030. Epub 2020 Jun 20.

Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, PR China; Engineering Research Center for Industrialization of Southern Medicinal Plants Resources of Hainan Province, Hainan Normal University, Haikou 571158, PR China; Key Laboratory of Southern Medicinal Plants Resources of Haikou City, Hainan Normal University, Haikou 571158, PR China; Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, Hainan Normal University, Haikou 571158, PR China. Electronic address:

Two new prenylated chromones, artoheterophines A (1) and B (2), five known prenylated chromones (3-7), as well as five known biogenetically related prenylated flavonoids (8-12) were isolated and characterized from the stems and leaves of A. heterophyllus. Their chemical structures were unambiguously determined through comprehensive spectral data analyses. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104030DOI Listing

In vitro inhibitory effects of Chinese bayberry (Myrica rubra Sieb. et Zucc.) leaves proanthocyanidins on pancreatic α-amylase and their interaction.

Bioorg Chem 2020 Jun 19;101:104029. Epub 2020 Jun 19.

College of Biosystems Engineering and Food Science, Zhejiang University, Zhejiang Key Laboratory for Agro-Food Processing, Fuli Institute of Food Science, Zhejiang R&D Center for Food Technology and Equipment, Hangzhou 310058, People's Republic of China; Ningbo Research Institute, Zhejiang University, Ningbo, 315100, People's Republic of China. Electronic address:

Chinese bayberry leaves proanthocyanidins (BLPs) belongs to the prodelphinidin category with potent EGCG unit, whose inhibition effect on α-amylase and their interaction were investigated by in vitro digestion and enzyme kinetic analysis, multi fluorescence spectroscopies (fluorescence quenching, synchronous fluorescence, and three-dimensional fluorescence), circular dichroism spectra, Fourier transform infrared spectroscopy and in silico modelling. The results revealed that BLPs was a mixed inhibitor to α-amylase with the IC value of 3.075 ± 0. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104029DOI Listing

Design, synthesis, and antitumor activity of novel compounds based on 1,2,4-triazolophthalazine scaffold: Apoptosis-inductive and PCAF-inhibitory effects.

Bioorg Chem 2020 Jun 17;101:104019. Epub 2020 Jun 17.

Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Nasr City 11884, Cairo, Egypt; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Horus University - Egypt, International Costal Road, New Damietta, Egypt. Electronic address:

The antitumor activity of newly synthesised triazolophthalazines (L-45 analogues) 10-32 was evaluated in human hepatocellular carcinoma (HePG-2), breast cancer (MCF-7), prostate cancer (PC3), and colorectal carcinoma (HCT-116) cells. Compounds 17, 18, 25, and 32 showed potent antitumor activity (IC, 2.83-13. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104019DOI Listing

Design, synthesis and neuropharmacological evaluation of new 2,4-disubstituted-1,5-benzodiazepines as CNS active agents.

Bioorg Chem 2020 Jun 16;101:104010. Epub 2020 Jun 16.

Department of Pharmaceutical Chemistry, Rajendra Institute of Technology & Sciences, Sirsa 125055, Haryana, India; Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Ghal Kalan, GT Road, Moga 142001, Punjab, India. Electronic address:

Benzodiazepines (BZDs) represent a class of privilege scaffold in the modern era of medicinal chemistry as CNS active agents and BZD based drugs are used to treat different psychotic disorders. Inspired from the therapeutic potential of BZDs as promising CNS active agents, in the present work three different series of 1,5-benzodiazepines bearing various substitutions at position 2 and 4 of the benzodiazepine core were synthesized by condensing different substituted chalcones with o-phenylenediamine in the presence of piperidine as a base catalyst. Structural characterization of title compounds was done by using various analytical techniques such as IR, NMR, elemental analysis and mass spectral data. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104010DOI Listing

Discovery of monoamine oxidase A inhibitory peptides from hairtail (Trichiurus japonicus) using in vitro simulated gastrointestinal digestion and in silico studies.

Bioorg Chem 2020 Jun 19;101:104032. Epub 2020 Jun 19.

College of Food Science and Engineering, South China University of Technology, Guangzhou 510640, China. Electronic address:

The aim of this study was to effectively obtain monoamine oxidase A (MAO-A) inhibitory peptides from in vitro simulated gastrointestinal digestion and to assess the correspondences between in silico prediction and in vitro confirmation. Fractions (<3 kDa) from ultrafiltration of pepsin and simulated gastrointestinal enzymes hydrolysates exhibited the highest MAO-A inhibitory activity with IC values of 0.61 and 2. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104032DOI Listing

Thiophene-based derivatives as anticancer agents: An overview on decade's work.

Bioorg Chem 2020 Jun 17;101:104026. Epub 2020 Jun 17.

Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Moga 142001, Punjab, India. Electronic address:

Heterocyclic compounds hold a pivotal place in medicinal chemistry due to their wide range of biological activities and thus, are exhaustively explored in the field of drug design and development. Continuous efforts are being carried out for the development of medicinal agents especially, for dreadful diseases like cancer. Thiophene, a sulfur containing heterocyclic scaffold, has emerged as one of the relatively well-explored scaffold for the development of library of molecules having potential anticancer profile. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104026DOI Listing

Discovery of tetrandrine derivatives as tumor migration, invasion and angiogenesis inhibitors.

Bioorg Chem 2020 Jun 17;101:104025. Epub 2020 Jun 17.

State Key Laboratory of Functions and Applications of Medicinal Plants, Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, PR China; School of Pharmacy, Guizhou Medical University, Guian New District, Guizhou, PR China. Electronic address:

Metastatic progression of cancer is a complex and clinically daunting process, with migration, invasion and angiogenesis being the key features. Tetrandrine (TET) is a typical dibenzylisoquinoline alkaloid with promising anti-tumor activity. In our previous work, a number of TET derivatives were designed and synthesized with obvious anti-proliferation activities against cancer cells, however, the anti-metastatic effects of these compounds were not evaluated. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104025DOI Listing

(3E,5E)-3,5-Bis(pyridin-3-methylene)-tetrahydrothiopyran-4-one enhances the inhibitory effect of gemcitabine on pancreatic cancer cells.

Bioorg Chem 2020 Jun 17;101:104022. Epub 2020 Jun 17.

School of Biotechnology and Health Sciences, Wuyi University, Jiangmen City 529020, China; International Healthcare Innovation Institute (Jiangmen), Jiangmen City, Guangdong Province 529020, China. Electronic address:

Gemcitabine (GEM) is a commonly used treatment for advanced pancreatic cancer. However, chemoresistance and toxic side effect limits its clinical success. In an earlier study, our laboratory found that the curcumin analogue, (3E,5E)-3,5-Bis(pyridin-3-methylene)-tetrahydrothiopyran-4-one (FN2) had strong inhibitory effect on human pancreatic cancer cells. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104022DOI Listing

Design, synthesis and anticonvulsant activity of new imidazolidindione and imidazole derivatives.

Bioorg Chem 2020 Jun 17;101:104020. Epub 2020 Jun 17.

Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University, Egypt.

New imidazolidindiones and tetra-substituted imidazole derivatives were designed, synthesized, and evaluated for the anticonvulsant activity through pentylenetetrazole (PTZ)-induced seizures and maximal electroshock (MES) tests using valproate sodium and phenytoin sodium as reference drugs, respectively. Most of the target compounds showed excellent activity against pentylenetetrazole (PTZ)-induced seizures with fair to no-activity against MES. Compounds 3d, 4e, 11b, and 11e showed higher activity (120%) than that of valproate sodium in PTZ model. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104020DOI Listing

Chemical constituents of Ligusticum chuanxiong and their anti-inflammation and hepatoprotective activities.

Bioorg Chem 2020 Jun 17;101:104016. Epub 2020 Jun 17.

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China. Electronic address:

Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104016DOI Listing

Antimicrobial and antiproliferative activity studies of some new quinoline-3-carbaldehyde hydrazone derivatives.

Bioorg Chem 2020 Jun 12;101:104014. Epub 2020 Jun 12.

Department of Medical Microbiology, Faculty of Medicine, Trakya University, Edirne, Turkey.

In this study, a total of 22 piece quinoline-3-carbaldehyde hydrazone derivative compounds were designed and synthesized, 2 of which were not original, their antimicrobial activities were determined with microdilution method and their in vitro cytotoxic effect was investigated in MCF-7 and A549 cells by MTT assay. When the activity results are examined, although the antimicrobial effects of quinoline derivatives, in general, are weaker than standard drugs; 3q5 and 3q6 against MRSA showed promising activity with MIC:16 µg/ml compared to reference drugs. Compounds generally showed weaker cytotoxic activity on the A549 and MCF-7 cell line. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104014DOI Listing

A Pt(IV)-based mononitro-naphthalimide conjugate with minimized side-effects targeting DNA damage response via a dual-DNA-damage approach to overcome cisplatin resistance.

Bioorg Chem 2020 Jun 12;101:104011. Epub 2020 Jun 12.

School of Pharmacy, Institute for Innovative Drug Design and Evaluation, Henan University, N. Jinming Ave, 475004 Kaifeng, China. Electronic address:

Platinum(Pt)(II) drugs and new Pt(IV) agents behave the dysregulation of apoptosis as the result of DNA damage repair and thus, are less effective in the treatment of resistant tumors. Herein, mononitro-naphthalimide Pt(IV) complex 10b with minimized side-effects was reported targeting DNA damage response via a dual-DNA-damage approach to overcome cisplatin resistance. 10b displayed remarkably evaluated antitumor (70. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104011DOI Listing

Design, synthesis, bioevaluation of LFC- and PA-tethered anthraquinone analogues of mitoxantrone.

Bioorg Chem 2020 Jun 10;101:104005. Epub 2020 Jun 10.

Key Laboratory of Chemistry and Chemical Biology (Ministry of Education), Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Ji'nan, Shandong 250012, China; Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji'nan, Shandong, 250002, China. Electronic address:

The clinical application of mitoxantrone (MTZ), a DNA-intercalating topoisomerase II (topo II) poison, has been largely limited by the risk of secondary tumor and severe myelosuppression. To develop more effective antineoplastic agents with less toxicity, a spectrum of anthraquinone analogues of MTZ were herein designed and synthesized based on the concept of 'enhancing protein backbone-binding', by rationally introducing hydrophobic long fatty acid chain (LFC) and hydrophilic polyamine (PA) components, which are reported to function as effective tumor-targeting tethers. The SAR exploration implicated that in our synthesized molecules, the introduction of both lipophilic LFC and hydrophilic PA fragment is plausibly beneficial to the anti-proliferative potency, with a certain degree of selectivity between the hematopoietic and solid malignant cells, which still need to be further accurately confirmed. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104005DOI Listing

The fatty acid amide hydrolase and cyclooxygenase-inhibitory properties of novel amide derivatives of carprofen.

Bioorg Chem 2020 Jun 20;101:104034. Epub 2020 Jun 20.

Department of Life and Environmental Sciences - Unit of Pharmaceutical, Pharmacological and Nutraceutical Sciences, University of Cagliari, Cagliari, Italy. Electronic address:

In experimental animals, inhibition of fatty acid amide hydrolase (FAAH) reduces the gastrointestinal damage produced by non-steroidal anti-inflammatory agents that act by inhibition of cyclooxygenase (COX). This suggests that compounds able to inhibit both enzymes may be potentially useful therapeutic agents. In the present study, we have investigated eight novel amide analogues of carprofen, ketoprofen and fenoprofen as potential FAAH/COX dual action inhibitors. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104034DOI Listing

Diversity-oriented generation and biological evaluation of new chemical scaffolds bearing a 2,2-dimethyl-2H-chromene unit: Discovery of novel potent ANO1 inhibitors.

Bioorg Chem 2020 Jun 8;101:104000. Epub 2020 Jun 8.

College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 21983, Republic of Korea. Electronic address:

Chemical territory bearing a 2,2-dimethyl-2H-chromene motif was expanded by utilizing an o-hydroxy aldehyde group of 5-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde as a synthetic handle to install distinctive morphology and functionality of each scaffold. Cell based assays and in silico docking analysis led us to discover that these new compounds exhibit inhibitory effect on anoctamin1 (ANO1). ANO1 is amplified and highly expressed in various carcinomas including prostate cancer, esophageal cancer, breast cancer, and pancreatic cancer. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104000DOI Listing

Development of pyrazolo[3,4-d]pyrimidine-6-amine-based TRAP1 inhibitors that demonstrate in vivo anticancer activity in mouse xenograft models.

Bioorg Chem 2020 Jun 15;101:103901. Epub 2020 Jun 15.

College of Pharmacy and Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, South Korea; Western Seoul Center, Korea Basic Science Institute, Seoul 03760, South Korea. Electronic address:

TNF Receptor Associated Protein 1 (TRAP1) is a mitochondrial paralog of Hsp90 related to the promotion of tumorigenesis in various cancers via maintaining mitochondrial integrity, reducing the production of reactive oxygen species, and reprogramming cellular metabolism. Consequently, Hsp90 and TRAP1 have been targeted to develop cancer therapeutics. Herein, we report a series of pyrazolo[3,4-d]pyrimidine derivatives that are mitochondria-permeable TRAP1 inhibitors. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103901DOI Listing

Design, synthesis, and cytotoxic screening of novel azole derivatives on hepatocellular carcinoma (HepG2 Cells).

Bioorg Chem 2020 Jun 3;101:103995. Epub 2020 Jun 3.

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo, Egypt.

Novel azole derivatives 3-30 were designed, synthesized, and screened for their antitumor activity on HepG2 cell line. The cytotoxicity screening demonstrated that imidazolone 8 and triazoles 25 and 29 exhibited more potent cytotoxic activities by 1.21-, 4. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103995DOI Listing

New nitroindazole-porphyrin conjugates: Synthesis, characterization and antibacterial properties.

Bioorg Chem 2020 Jun 3;101:103994. Epub 2020 Jun 3.

Laboratory of Organic and Analytic Chemistry, Faculty of Sciences and Technics, Sultan Moulay Slimane University, BP 523, 2300 Beni-Mellal, Morocco. Electronic address:

The synthesis of new porphyrin-indazole hybrids by a Knoevenagel condensation of 2-formyl-5,10,15,20-tetraphenylporphyrin and N-methyl-nitroindazolylacetonitrile derivatives is reported. The target compounds were isolated in moderate to good yields (32-57%) and some of the isolated porphyrin-indazole conjugates showed good performance in the generation of singlet oxygen when irradiated with visible light. Their efficiency as photosensitizers in the photoinactivation of methicillin resistant Staphylococcus aureus-MRSA was evaluated. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103994DOI Listing

Discovery and optimization of 3-thiophenylcoumarins as novel agents against Parkinson's disease: Synthesis, in vitro and in vivo studies.

Bioorg Chem 2020 Jun 2;101:103986. Epub 2020 Jun 2.

Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain; CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal. Electronic address:

Monoamine oxidase B (MAO-B) inhibitors are still receiving great attention as promising therapeutic agents for central nervous system disorders. This study explores, for the first time, the potential of 3-thiophenylcoumarins as in vitro and in vivo agents against Parkinsońs disease. Twelve compounds were synthesized via Perkin-Oglialoro reaction, and in vitro evaluation of six hydroxylated molecules was performed. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103986DOI Listing

Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification.

Bioorg Chem 2020 Jun 8;101:103999. Epub 2020 Jun 8.

Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address:

In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103999DOI Listing
June 2020
2.152 Impact Factor

Bisthioureas of pimelic acid and 4-methylsalicylic acid derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP) and intestinal alkaline phosphatase (IAP): Synthesis and molecular docking studies.

Bioorg Chem 2020 Jun 3;101:103996. Epub 2020 Jun 3.

Center for Advanced Drug Research, COMSATS University Islamabad, Abbottabad Campus, Abbottabad 22060, Pakistan. Electronic address:

Alkaline phosphatases (ALPs) are membrane bound metalloenzymes, distributed all over the body. Recent studies have revealed that by targeting ALPs can lead towards the treatment of many deadliest diseases including cardiac, cancerous and brain diseases. Thioureas and their derivatives are of considerable significance and are privileged scaffolds in medicinal chemistry. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103996DOI Listing

Synthesis, α-glucosidase inhibition and in silico studies of some 4-(5-fluoro-2-substituted-1H-benzimidazol-6-yl)morpholine derivatives.

Bioorg Chem 2020 Jun 10;101:104002. Epub 2020 Jun 10.

Department of Chemistry, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, Rize, Turkey. Electronic address:

In this study, a new series of 4-(5-fluoro-2-substituted-1H-benzimidazol-6-yl)morpholine derivatives has been synthesized and screened for their α-glucosidase inhibitory potential. All molecules showed a considerable α-glucosidase inhibitory potential with IC values ranging from 20.46 ± 0. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.104002DOI Listing

New complex polycyclic compounds: Synthesis, antiproliferative activity and mechanism of action.

Bioorg Chem 2020 Jun 1;101:103989. Epub 2020 Jun 1.

Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), Medicinal Chemistry and Pharmaceutical Technologies Section - University of Palermo, Via Archirafi 32, 90123 Palermo, Italy.

Polycyclic or O-glycoconiugate polycyclic compounds 1a-g were previously tested for their in vitro antiproliferative activity. In this series of compounds, activity increases as log P decreases. Specifically, compounds 1d and 1g showed lower log P values together with the best antiproliferative profiles. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103989DOI Listing

Design, synthesis, and biological evaluation of tetrahydroquinolin derivatives as potent inhibitors of CBP bromodomain.

Bioorg Chem 2020 Jun 2;101:103991. Epub 2020 Jun 2.

Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China; University of Chinese Academy of Sciences, 19 Yuquan Road, Beijing 100049, China; Open Studio for Druggability Research of Marine Natural Products, Pilot National Laboratory for Marine Science and Technology (Qingdao), 1 Wenhai Road, Aoshanwei, Jimo, Qingdao 266237, China. Electronic address:

CREB-binding protein (CBP) is a large multi-domain protein containing a HAT domain catalyzing transacetylation and a bromodomain responsible for acetylated lysine recognition. CBPs could act as transcription co-activators to regulate gene expression and have been shown to play a significant role in the development and progression of many cancers. Herein, through in silico screening two hit compounds with tetrahydroquinolin methyl carbamate scaffold were discovered, among which DC-CPin7 showed an in vitro inhibitory activity with the TR-FRET IC value of 2. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103991DOI Listing

Development of broad-spectrum enterovirus antivirals based on quinoline scaffold.

Bioorg Chem 2020 Jun 1;101:103981. Epub 2020 Jun 1.

Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, United States. Electronic address:

Non-polio enteroviruses such as enterovirus A71 (EV-A71), EV-D68, and coxsackievirus B3 (CVB3) are significant human pathogens with disease manifestations ranging from mild flu-like symptoms to more severe encephalitis, myocarditis, acute flaccid paralysis/myelitis, and even death. There is currently no effective antivirals to prevent or treat non-polio enterovirus infection. In this study, we report our progress in developing potent and broad-spectrum antivirals against these non-polio enteroviruses. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103981DOI Listing

Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents.

Bioorg Chem 2020 Jun 2;101:103960. Epub 2020 Jun 2.

Department of Life Sciences and Biotechnology, Master Course in Cosmetic Science and Technologies, University of Ferrara, via L. Borsari 46, 44121 Ferrara, Italy.

Oxidative stress is the product or aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized via condensation reaction between 2-aminothiophenols and different benzaldehydes. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103960DOI Listing

Synthesis and anti-parasitic activity of achiral N-benzylated phosphoramidic acid derivatives.

Bioorg Chem 2020 May 16;101:103947. Epub 2020 May 16.

Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa; Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa. Electronic address:

Synthetic pathways have been developed to access a series of N-benzylated phosphoramidic acid derivatives as novel, achiral analogues of the established Plasmodium falciparum 1-deoxy-d-xylulose-5-phosphate reductase (PfDXR) enzyme inhibitor, FR900098. Bioassays of the targeted compounds and their synthetic precursors have revealed minimal antimalarial activity but encouraging anti-trypanosomal activity - in one case with an IC value of 5.4 µM against Trypanosoma brucei, the parasite responsible for Nagana (African cattle sleeping sickness). Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103947DOI Listing

Recent progress of antibacterial natural products: Future antibiotics candidates.

Bioorg Chem 2020 May 20;101:103922. Epub 2020 May 20.

School of Life Science and Technology, Weifang Medical University, Shandong, China(1); College of Chemistry & Pharmacy, Northwest A&F University, Shaanxi, China(1). Electronic address:

The discovery of novel antibacterial molecules plays a key role in solving the current antibiotic crisis issue. Natural products have long been an important source of drug discovery. Herein, we reviewed 256 natural products from 11 structural classes in the period of 2016-01/2020, which were selected by SciFinder with new compounds or new structures and MICs lower than 10 μg/mL or 10 μM as criterions. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103922DOI Listing

Synthesis and molecular docking study of new pyrazole derivatives as potent anti-breast cancer agents targeting VEGFR-2 kinase.

Bioorg Chem 2020 May 16;101:103916. Epub 2020 May 16.

Biochemistry Department, Genetic Engineering and Biotechnology Research Division, National Research Centre, 33 El Bohouth St., Dokki, Giza, P.O. Box 12622, Egypt.

Based on the previous studies that revealed the valuable role of pyrazole scaffold in cancer management and VEGFR-2 inhibition, a new set of pyrazole conjugated with pyrazoline, triazolopyrimidine and pyrazolone moieties were synthesized and investigated for their anticancer efficiency against human breast cancer MCF-7. The anticancer screening revealed the significant sensitivity of breast carcinoma towards compounds 4b, 5c, 6c, 7b, 7c and 12c with IC values ranging from 16.50 - 26. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103916DOI Listing
May 2020
2.152 Impact Factor

Synthesis of furocoumarin-stilbene hybrids as potential multifunctional drugs against multiple biochemical targets associated with Alzheimer's disease.

Bioorg Chem 2020 Jun 3;101:103997. Epub 2020 Jun 3.

Department of Life & Consumer Sciences, College of Agriculture and Environmental Sciences, University of South Africa, Private Bag X06, Florida 1710, South Africa.

A series of furocoumarin-stilbene hybrids has been synthesized and evaluated in vitro for inhibitory effect against acetylcholinesterase (AChE), butyrylcholinestarase (BChE), β-secretase, cyclooxygenase-2 (COX-2), and lipoxygenase-5 (LOX-5) activities including free radical-scavenging properties. Among these hybrids, 8-(3,5-dimethoxyphenyl)-4-(3,5-dimethoxystyryl)furochromen-2-one 4h exhibited significant anticholinesterase activity and inhibitory effect against β-secretase, COX-2 and LOX-5 activities. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and an in vitro cell-based antioxidant activity assay involving lipopolysaccharide induced reactive oxygen species production revealed that 4h has capability of scavenging free radicals. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103997DOI Listing

Novel molecular discovery of promising amidine-based thiazole analogues as potent dual Matrix Metalloproteinase-2 and 9 inhibitors: Anticancer activity data with prominent cell cycle arrest and DNA fragmentation analysis effects.

Bioorg Chem 2020 Jun 2;101:103992. Epub 2020 Jun 2.

Pharmacognosy and Pharmaceutical Chemistry Department, College of Pharmacy, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia; Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, 11884 Nasr City, Cairo, Egypt.

Thiazole derivatives are known to possess various biological activities such as antiparasitic, antifungal, antimicrobial and antiproliferative activities. Matrix metalloproteinases (MMPs) are important protease target involved in tumor progression including angiogenesis, tissue invasion, and migration. Therefore, MMPs have also been reported as potential diagnostic and prognostic biomarkers in many types of cancer. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103992DOI Listing

Molecular mechanism of action of new 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles with cytotoxic and selective effect against oral squamous cell carcinoma.

Bioorg Chem 2020 Jun 1;101:103984. Epub 2020 Jun 1.

Universidade Federal Fluminense, Campus Universitário de Nova Friburgo, Departamento de Ciência Básica, CEP 28625-650, Nova Friburgo-RJ, Brazil. Electronic address:

The oral squamous cell carcinoma (OSCC) stands out as a public health problem due to its high incidence and low survival rate, despite advances in diagnosis and treatment. Moreover, the most commonly chemotherapeutic agents for OSCC, such as carboplatin and cisplatin, generate important side effects, evidencing the urgency in developing new drugs. Naphthoquinones are an important class of natural products or synthetic compounds with cytotoxic effect demonstrated on different cancer types. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103984DOI Listing

Design, synthesis and biological evaluation of novel chroman derivatives as non-selective acetyl-CoA carboxylase inhibitors.

Bioorg Chem 2020 May 15;101:103943. Epub 2020 May 15.

Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China. Electronic address:

Acetyl-CoA carboxylases (ACCs) are the rate-limiting enzymes in the de no lipogenesis, which play an important role in the synthesis and oxidation of fatty acid. Recent research reveals that ACCs are tightly relevant to many kinds of metabolic diseases and cancers. In this study, we synthesized a series of chroman derivatives and evaluated their ACCs inhibitory activities, obtaining compound 4s with IC value of 98. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103943DOI Listing

Efficient biogenesis of ZnO nanoparticles using extracellular extract of Saccharomyces cerevisiae : Evaluation of photocatalytic, cytotoxic and other biological activities.

Bioorg Chem 2020 Jun 8;101:103998. Epub 2020 Jun 8.

Department of Medicinal Plant, Amol University of Special Modern Technologies, Amol, Iran.

This research aimed to synthesize zinc oxide nanoparticles (ZnO NPs) using an extracellular extract of Saccharomyces cerevisiae. The physical characteristics of the biosynthesized NPs were studied using XRD, FTIR, FESEM, and EDS. Microscopic study and spectroscopic examination depicted spherical ZnO NPs < 30 nm diameter in size, relatively stable, and bearing a hexagonal phase. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103998DOI Listing

Synthesis, anti-microbial and anti-inflammatory activities of 18β-glycyrrhetinic acid derivatives.

Bioorg Chem 2020 Jun 1;101:103985. Epub 2020 Jun 1.

Faculty of Pharmaceutical Engineering, School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou 510006, People's Republic of China. Electronic address:

Thirteen 18β-glycyrrhetinic acid (GA) derivatives were obtained by reduction at C-11 position, oxidation at C-3 position and condensation at C-2 position of GA. Anti-microbial activity evaluation indicated that compounds 04, 05, 10, 13 and 14 showed more potent inhibitory activity against Staphylococcus aureus subsp. aureus, Staphylococcus epidermidis, Staphylococcus aureus than GA, especially compound 10, the inhibitory activity against Staphylococcus epidermidis was equaled with Ampicillin. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103985DOI Listing
June 2020
2.152 Impact Factor

Synthesis and screening of (E)-3-(2-benzylidenehydrazinyl)-5,6-diphenyl-1,2,4-triazine analogs as novel dual inhibitors of α-amylase and α-glucosidase.

Bioorg Chem 2020 Jun 1;101:103979. Epub 2020 Jun 1.

PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi-75280, Pakistan.

(E)-3-(2-Benzylidenehydrazinyl)-5,6-diphenyl-1,2,4-triazines analogs 1-27 were synthesized by multi-step reaction scheme and subjected to in vitro inhibitory screening against α-amylase and α-glucosidase enzymes. Out of these twenty-seven synthetic analogs, ten compounds 14-17, 19, and 21-25 are structurally new. All compounds exhibited good to moderate inhibitory potential in terms of IC values ranging (IC = 13. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103979DOI Listing

Further polyoxygenated cembranoids from South China Sea soft coral Sarcophyton ehrenbergi.

Bioorg Chem 2020 Jun 2;101:103993. Epub 2020 Jun 2.

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shaoshan Road, Changsha 410004, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. Electronic address:

Eleven new cembrane diterpenes, namely, sarcoehrenins A-J (1-9, 11) and (2S,11S,12S)-isosarcophytoxide (10), along with six known compounds, gibberosene B (12), (13S)-cembra-1,3,7,11-tetraen-13-ol (13), (+)-sarcophtol (14), cembrene-C (15), (1R,4R,2E,7E,11E)-cembra-2,7,11-trien-4-ol (16) and (1S,4R,2E,7E,11E)-cembratrien-4-ol (17) were isolated from the soft coral Sarcophyton ehrenbergi collected from Weizhou Island, Beibu Gulf, South China Sea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. The absolute configuration of compound 2 was established by the modified Mosher's method in association with TDDFT ECD calculation, while the absolute configuration of compound 3 was assigned by TDDFT ECD approach. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103993DOI Listing

Synthetic approaches, anticancer potential, HSP90 inhibition, multitarget evaluation, molecular modeling and apoptosis mechanistic study of thioquinazolinone skeleton: Promising antibreast cancer agent.

Bioorg Chem 2020 Jun 1;101:103987. Epub 2020 Jun 1.

Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, P.O. Box 35516, Mansoura, Egypt.

New series of compounds bearing 2-thioquinazolinone scaffold were designed, synthesized as HSP90 inhibitors. Anti-proliferative activity of the synthesized compounds was evaluated against HCT-116, Hela and MCF-7 cell lines and compound 5k was found to be the most active member of the entire study with IC of 4.47, 7. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103987DOI Listing

Synthesis, pharmacological evaluation and mechanistic study of scutellarin methyl ester -4'-dipeptide conjugates for the treatment of hypoxic-ischemic encephalopathy (HIE) in rat pups.

Bioorg Chem 2020 Jun 1;101:103980. Epub 2020 Jun 1.

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550004, Guizhou, China; School of Pharmacy, Guizhou Medical University, Guiyang 550004, China; National Engineering Research Center of Miao's Medicines & Engineering Research Center for the Development and Application of Ethnic Medicine and TCM, Ministry of Education, Guiyang 550004, Guizhou, China. Electronic address:

A series of novel scutellarin methyl ester-4'-dipeptide conjugates exhibiting active transport characteristics and protection against pathological damage caused by hypoxic-ischemic encephalopathy (HIE) were successfully designed and synthesized. The physiochemical properties of the obtained compounds, as well as the Caco-2 cell-based permeability and uptake into hPepT1-MDCK cells were evaluated using various analytical methods. Scutellarin methyl ester-4'-Val-homo-Leu dipeptide (5k) was determined as the optimal candidate with a high apparent permeability coefficient (P) of 1. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103980DOI Listing
June 2020
2.152 Impact Factor

Design, synthesis, and in vitro evaluation of novel triazole analogues featuring isoxazole moieties as antifungal agents.

Bioorg Chem 2020 Jun 2;101:103982. Epub 2020 Jun 2.

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, China. Electronic address:

In order to develop novel antifungal agents, based on our previous work, a series of (2R,3R)-3-((3-substitutied-isoxazol-5-yl)methoxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol (a1-a26) were designed and synthesized. All of the compounds exhibited good in vitro antifungal activities against eight human pathogenic fungi. Among them, compound a6 showed excellent inhibitory activity against Candida albicans and Candida parasilosis with MIC values of 0. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103982DOI Listing

Interaction of dicentrinone, an antitrypanosomal aporphine alkaloid isolated from Ocotea puberula (Lauraceae), in cell membrane models at the air-water interface.

Bioorg Chem 2020 Jun 1;101:103978. Epub 2020 Jun 1.

Department of Chemistry, Federal University of São Paulo, Diadema, SP, Brazil. Electronic address:

In the present work, the oxoaporphine alkaloid dicentrinone was isolated, for the first time, from leaves of Ocotea puberula (Lauraceae). This alkaloid exhibited antiparasitic activity against trypomastigote forms of Trypanosoma cruzi (IC of 16.4 ± 1. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103978DOI Listing

Exploration of certain 1,3-oxazole- and 1,3-thiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.

Bioorg Chem 2020 Jun 1;101:103988. Epub 2020 Jun 1.

Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, Viet Nam. Electronic address:

Several novel series of hydroxamic acids bearing 2-benzamidooxazole/thiazole (5a-g, 6a-g) or 2-phenylsulfonamidothiazole (8a-c) were designed and synthesized. The compounds were obtained straightforwards via a two step pathway, starting from commercially available ethyl 2-aminooxazole-4-carboxylate or ethyl 2-aminothiazole-4-carboxylate. Biological evaluation showed that these hydroxamic acids generally exhibited good cytotoxicity against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI-H23, lung cancer), with IC values in low micromolar range and comparable to that of SAHA. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103988DOI Listing

Efficient biocatalytic strategy for one-pot Biginelli reaction via enhanced specific effects of microwave in a circulating reactor.

Bioorg Chem 2020 Jun 1;101:103949. Epub 2020 Jun 1.

State Key Laboratory of Nuclear Resources and Environment, School of nuclear science and engineering, East China University of Technology, 418 Guanglan Road, Nanchang 330013, PR China; Department of Applied Chemistry, East China University of Technology, 418 Guanglan Road, Nanchang 330013, PR China. Electronic address:

A one-pot efficient biocatalytic strategy for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones was developed in a circulating microwave reactor selecting α-chymotrypsin as the promiscuous biocatalyst. In the circulating reaction system, the combination of microwave heating and external cooling could avoid the denaturation and inactivation of enzyme, and greatly improved the radiation power of microwave, thus improving the specific effects of microwave. During the reaction process, the microwave radiation power was automatically adjusted by adjusting the speed of the reaction mixture circulation. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103949DOI Listing

Sesquiterpenoids isolated from the flower of Inula japonica as potential antitumor leads for intervention of paclitaxel-resistant non-small-cell lung cancer.

Bioorg Chem 2020 May 24;101:103973. Epub 2020 May 24.

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:

Three new sesquiterpene lactone dimers (1-3) were isolated from the flowers of Inula japonica together with twenty-two known sesquiterpene derivatives (4-25). Their structures were established on the basis of detailed spectroscopic analyses. All isolates were evaluated for their antiproliferative activities against paclitaxel-resistant human non-small-cell lung cancer cell line A549/PTX. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103973DOI Listing

Corrigendum to "Hyperpatulols A-I, spirocyclic acylphloroglucinol derivatives with anti-migration activities from the flowers of hypericum patulum" [Bioorg. Chem. 87 (2019) 409-416].

Bioorg Chem 2020 Jun 5:103990. Epub 2020 Jun 5.

Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China. Electronic address:

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http://dx.doi.org/10.1016/j.bioorg.2020.103990DOI Listing
June 2020
2.152 Impact Factor

Nitric oxide inhibitory iridoids as potential anti-inflammatory agents from Valeriana jatamansi.

Bioorg Chem 2020 May 25;101:103974. Epub 2020 May 25.

State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Tianjin Key Laboratory of Molecular Drug Research, and Drug Discovery Center for Infectious Disease, Nankai University, Tianjin 300350, People's Republic of China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China. Electronic address:

Five new iridoids, jatadomins A-E (1-5), together with six known analogues (6-11) and one known sesquiterpenoid (12), were isolated from the roots of Valeriana jatamansi Jones. Their structures were determined by analysis of their NMR, HRESIMS, and electronic circular dichroism calculations (ECD) data. The biological evaluation revealed that compounds 1-6 had anti-inflammatory activities by inhibiting nitric oxide (NO) release in LPS-induced murine microglial BV-2 cells, with IC values of 24. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103974DOI Listing

Design, synthesis, mechanistic studies and in silico ADME predictions of benzimidazole derivatives as novel antifungal agents.

Bioorg Chem 2020 May 22;101:103956. Epub 2020 May 22.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ain Shams University, Abbassia, Cairo 11566, Egypt.

Herein, novel three series of benzimidazole scaffold bearing hydrazone, 1,2,4-triazole and 1,3,4-oxadiazole moieties 1-3, 4a-j, 6a-c and 7 derivatives were designed, synthesized and evaluated for their antimicrobial activity. The structures of the prepared compounds were assigned using different spectroscopic techniques such as IR, H NMR, C NMR and elemental analyses. Compounds 3, 4a, 4e and 4f exhibited remarkable antifungal activity against C. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103956DOI Listing
May 2020
2.152 Impact Factor

New anti-neuroinflammatory steroids against LPS induced NO production in BV2 microglia cells by microbial transformation of isorhodeasapogenin.

Bioorg Chem 2020 Apr 22;101:103870. Epub 2020 Apr 22.

School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China; Guangdong Engineering Research Center for Lead Compounds & Drug Discovery, Guangzhou 510006, China. Electronic address:

Microbial transformation of isorhodeasapogenin (1), the major steroidal sapogenin of Tupistra chinensis, was performed with the fungus Syncephalastrum racemosum (AS 3.264). As a result, nine new biotransformation metabolites (2-10) were isolated and their structures were elucidated by spectroscopic analysis. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103870DOI Listing

Densely functionalized cinnolines: Controlled microwave-assisted facile one-pot multi-component synthesis and in vitro anticancer activity via apoptosis induction.

Bioorg Chem 2020 May 23;101:103932. Epub 2020 May 23.

Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt.

There is an urging continuous need for novel anti-cancer agents due to persistent chemoresistance. Herein, newly synthesized cinnolines are evaluated for their possible anticancer activities and suggested mechanisms. In the current study, a simple and efficient synthesis of densely functionalized cinnolines has been developed that relied on multi-component reaction of ethyl 5-cyano-4-methyl-1-aryl-6-oxo-1,6-dihydropyridazine-3-carboxylates with aromatic aldehydes and nitromethane in dioxane/pipridine under controlled microwave heating. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103932DOI Listing

Design, synthesis, molecular docking and antiproliferative activity of some novel benzothiazole derivatives targeting EGFR/HER2 and TS.

Bioorg Chem 2020 May 26;101:103976. Epub 2020 May 26.

Department of Medicinal Chemistry, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt.

Multi-targeted anticancer drugs are in focus as a promising research topic. A new series of benzothiazoles hybridized with pyrimidine moiety was designed and synthesized using the lead compound 4a. Various chemical modifications on the pyrimidine ring of 4a at four different positions were done in a trial to get new multi-targeted anticancer agents. Read More

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http://dx.doi.org/10.1016/j.bioorg.2020.103976DOI Listing