4,204 results match your criteria Archiv Der Pharmazie[Journal]

Design, synthesis, and molecular docking of novel 3,5-disubstituted-1,3,4-oxadiazole derivatives as iNOS inhibitors.

Arch Pharm (Weinheim) 2021 May 9:e2000469. Epub 2021 May 9.

Department of Pharmacology, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.

To obtain new anti-inflammatory agents, recent studies have aimed to replace the carboxylate functionality of nonsteroidal anti-inflammatory drugs with less acidic heterocyclic bioisosteres like 1,3,4-oxadiazole to protect the gastric mucosa from free carboxylate moieties. In view of these observations, we designed and synthesized a series of 3,5-disubstituted-1,3,4-oxadiazole derivatives as inhibitors of prostaglandin E (PGE ) and NO production with an improved activity profile. As initial screening, and to examine the anti-inflammatory activities of the compounds, the inhibitions of the productions of lipopolysaccharide-induced NO and PGE in RAW 264. Read More

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Growth factor mimetics for skin regeneration: In vitro profiling of primary human fibroblasts and keratinocytes.

Arch Pharm (Weinheim) 2021 May 8:e2100082. Epub 2021 May 8.

Department of Biochemistry, Radboud Institute for Molecular Life Sciences, Radboud University Medical Center, Nijmegen, The Netherlands.

Small molecules have gained considerable interest in regenerative medicine, as they can effectively modulate cell fates in a spatiotemporal controllable fashion. A continuous challenge in the field represents genuine mimicry or activation of growth factor signaling with small molecules. Here, we selected and profiled three compounds for their capacity to directly or indirectly activate endogenous FGF-2, VEGF, or SHH signaling events in the context of skin regeneration. Read More

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Pyridine-derived VEGFR-2 inhibitors: Rational design, synthesis, anticancer evaluations, in silico ADMET profile, and molecular docking.

Arch Pharm (Weinheim) 2021 May 5:e2100085. Epub 2021 May 5.

Department of Pharmaceutical Medicinal Chemistry and Drug Design, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo, Egypt.

Novel pyridine-derived compounds (5-19) were designed and synthesized, and their anticancer activities were evaluated against HepG2 and MCF-7 cells, targeting the VEGFR-2 enzyme. Compounds 10, 9, 8, and 15 were found to be the most potent derivatives against the two cancer cell lines, HepG2 and MCF-7, respectively, with IC  = 4.25 and 6. Read More

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Synthesis of 5H-indeno[1,2-b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines.

Arch Pharm (Weinheim) 2021 Apr 30:e2100092. Epub 2021 Apr 30.

Organic Synthesis Laboratory, Faculty of Pharmacy, Central University of Venezuela, Caracas, Venezuela.

This study describes the direct synthesis of 2-amino-4-(phenylsubstituted)-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives 5-21, through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC-3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC-3 and LNCaP human cell lines. Read More

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Structural and biological aspects of natural bridged macrobicyclic peptides from marine resources.

Arch Pharm (Weinheim) 2021 Apr 29:e2100034. Epub 2021 Apr 29.

Department of Pharmaceutics, Nootan Pharmacy College, Faculty of Pharmacy, Sankalchand Patel University, Visnagar, Mehsana, Gujarat, India.

Among peptide-based drugs, naturally occurring bicyclic compounds have been established as molecules with unique therapeutic potential. The diverse pharmacological activities associated with bicyclic peptides from marine tunicates, sponges, and bacteria render them suitable to be employed as effective surrogate between complex and small therapeutic moieties. Bicyclic peptides possess greater conformational rigidity and higher metabolic stability as compared with linear and monocyclic peptides. Read More

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Synthesis of new 1,2,4-triazole-(thio)semicarbazide hybrid molecules: Their tyrosinase inhibitor activities and molecular docking analysis.

Arch Pharm (Weinheim) 2021 Apr 26:e2100058. Epub 2021 Apr 26.

Computer-Aided Drug Discovery Laboratory, Department of Pharmacology, Faculty of Pharmacy, Bezmialem Vakif University, Istanbul, Turkey.

Tyrosinase inhibition is very important in controlling melanin synthesis. If melanin synthesis is not controlled in metabolism, an unwanted increase in melanin synthesis occurs. As melanin plays a role in the formation of skin color, its unusual levels cause some skin disorders such as pregnancy scars, age spots, and especially skin cancer (melanoma). Read More

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Toad venom: A comprehensive review of chemical constituents, anticancer activities, and mechanisms.

Arch Pharm (Weinheim) 2021 Apr 22:e2100060. Epub 2021 Apr 22.

College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan, China.

Toad venom, a traditional natural medicine, has been used for hundreds of years in China for treating different diseases. Many studies have been performed to elucidate the cardiotonic and analgesic activities of toad venom. Until the last decade, an increasing number of studies have documented that toad venom is a source of lead compound(s) for the development of potential cancer treatment drugs. Read More

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Hybridization-based design of novel anticholinesterase indanone-carbamates for Alzheimer's disease: Synthesis, biological evaluation, and docking studies.

Arch Pharm (Weinheim) 2021 Apr 19:e2000453. Epub 2021 Apr 19.

Biotechnology Research Center, Tabriz University of Medical Sciences, Tabriz, Iran.

Inspired by the structures of donepezil and rivastigmine, a novel series of indanone-carbamate hybrids was synthesized using the pharmacophore hybridization-based design strategy, and their biological activities toward acetylcholinesterase (AChE) and butyrylcholinesterase were evaluated. Among the synthesized compounds, 4d and 4b showed the highest AChE inhibitory activities with IC values in the micromolar range (compound 4d: IC  = 3.04 μM; compound 4b: IC  = 4. Read More

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Synthesis and biological evaluation of new coumarin derivatives as cytotoxic agents.

Arch Pharm (Weinheim) 2021 Apr 19:e2100029. Epub 2021 Apr 19.

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

New coumarin derivatives 9a-f, 10a-e, and 11a-f were synthesized and evaluated for their cytotoxic activity against a human breast cancer cell line (MCF-7). All compounds exhibited good activity in the nanomolar range, using doxorubicin and erlotinib as positive controls. The most active compound 9d with IC of 21 nM was tested against the HCT-116, HepG-2, A549, and SGC-7901 cell lines, with IC values of 0. Read More

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Cytotoxic and antimicrobial potential of benzimidazole derivatives.

Arch Pharm (Weinheim) 2021 Apr 19:e2100076. Epub 2021 Apr 19.

Department of Biology, Faculty of Arts and Sciences, İnönü University, Malatya, Turkey.

New benzimidazole derivatives were synthesized and their structures were characterized by spectroscopic and microanalysis techniques. The cytotoxic properties of ten benzimidazole derivatives, five of which were synthesized in our previous studies, were determined against the lung cancer cell line, A549, and the healthy lung epithelial cell line, BEAS-2B. Among the ten compounds tested, based on the 72-h incubation results, compound 12 was the most cytotoxic against the A549 cell line, whereas against the BEAS-2B cell line, it was as cytotoxic as cisplatin. Read More

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Design, synthesis, and antiproliferative effect of 2,9-bis[4-(pyridinylalkylaminomethyl)phenyl]-1,10-phenanthroline derivatives on human leukemic cells by targeting G-quadruplex.

Arch Pharm (Weinheim) 2021 Apr 14:e2000450. Epub 2021 Apr 14.

Cellules souches hématopoïétiques normales et leucémiques, UFR des Sciences Pharmaceutiques, Université Bordeaux, INSERM, U1035, Bordeaux, France.

Current multiagent chemotherapy regimens have improved the cure rate in acute leukemia patients, but they are highly toxic and poorly efficient in relapsed patients. To improve the treatment approaches, new specific molecules are needed. The G-quadruplexes (G4s), which are noncanonical nucleic acid structures found in specific guanine-rich DNA or RNA, are involved in many cellular events, including control of gene expression. Read More

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In vitro and in vivo evaluation of a water-in-oil microemulsion of platycodin D.

Arch Pharm (Weinheim) 2021 Apr 12:e2000497. Epub 2021 Apr 12.

Department of Pharmacy, Jiangsu Ocean University, Lianyungang, Jiangsu, China.

Platycodin D (PD) is the active metabolite of Platycodon grandiflorum. The main purpose of this study was to develop and evaluate a water-in-oil (W/O) microemulsion formulation of PD (PD-ME). The PD-ME was successfully prepared by the water titration method at K  = 2, to draw the pseudoternary phase diagrams. Read More

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Synthesis and biological evaluation of new 4-oxo-thiazolidin-2-ylidene derivatives as antimicrobial agents.

Arch Pharm (Weinheim) 2021 Apr 7:e2100037. Epub 2021 Apr 7.

Department of Organic Chemistry, Ivan Franko National University of Lviv, Lviv, Ukraine.

In this study, an efficient synthesis and the antimicrobial activity evaluation of some 4-oxo-thiazolidin-2-ylidene derivatives are presented. The structures of the target substances were confirmed by using H and C nuclear magnetic resonance spectroscopy, mass spectrometry, infrared spectroscopy, and elemental analysis. The synthesized compounds were evaluated for antimicrobial activity against five bacterial strains (Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Staphylococcus aureus) and two fungal strains (Candida albicans and Cryptococcus neoformans). Read More

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Design, synthesis, docking, ADMET profile, and anticancer evaluations of novel thiazolidine-2,4-dione derivatives as VEGFR-2 inhibitors.

Arch Pharm (Weinheim) 2021 Mar 31:e2000491. Epub 2021 Mar 31.

Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy (Boys), Al-Azhar University, Nasr City, Cairo, Egypt.

The anticancer activity of novel thiazolidine-2,4-diones was evaluated against HepG2, HCT-116, and MCF-7 cells. Among the tested cancer cell lines, HCT-116 was the most sensitive one to the cytotoxic effect of the new derivatives. In particular, compounds 18, 11, and 10 were found to be the most potent derivatives among all the tested compounds against the HepG2, HCT-116, and MCF-7 cancer cell lines, with IC values ranging from 38. Read More

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Design and synthesis of benzenesulfonamide-linked imidazo[2,1-b][1,3,4]thiadiazole derivatives as carbonic anhydrase I and II inhibitors.

Arch Pharm (Weinheim) 2021 Mar 24:e2100028. Epub 2021 Mar 24.

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad, Telangana, India.

A novel series of imidazothiadiazole-linked benzenesulfonamide derivatives (5a-t) was synthesized and subjected for screening against the four physiologically and pharmacologically relevant human carbonic anhydrase (hCA) isoforms: hCA I, II, VA, and IX. The compounds selectively inhibited hCA I and II over hCA VA and IX. Furthermore, among the two cytosolic isoforms, hCA II was more effectively inhibited as compared with hCA I. Read More

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1,3,5-Triazine: A versatile pharmacophore with diverse biological activities.

Arch Pharm (Weinheim) 2021 Mar 24:e2000363. Epub 2021 Mar 24.

Drug Design and Discovery Laboratory, Department of Pharmaceutical Sciences, Sam Higginbottom University of Agriculture, Technology, and Sciences, Allahabad, Uttar Pradesh, India.

1,3,5-Triazine and its derivatives have been the epicenter of chemotherapeutic molecules due to their effective biological activities, such as antibacterial, fungicidal, antimalarial, anticancer, antiviral, antimicrobial, anti-inflammatory, antiamoebic, and antitubercular activities. The present review represents a summarized report of the crucial biological activities possessed by substituted 1,3,5-triazine derivatives, with special attention to the most potent compounds. Read More

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Facile synthesis of C6-substituted benz[4,5]imidazo[1,2-a]quinoxaline derivatives and their anticancer evaluation.

Arch Pharm (Weinheim) 2021 Mar 22:e2000393. Epub 2021 Mar 22.

Department of Chemistry and Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, India.

Cancer remains a leading cause of death worldwide, resulting in continuous efforts to discover and develop highly efficacious anticancer drugs. High-throughput screening of heterocyclic compound libraries is one of the promising approaches that provided several new lead molecules with a novel mechanism of action. On the basis of the promising anticancer potential of imidazoquinoxaline as well as the structurally similar imidazoquinoline-derived scaffold, we prepared a set of C6-substituted benzimidazo[1,2-a]quinoxaline derivatives via two novel synthetic routes using commercially available starting materials, with good to excellent yields and evaluated their anticancer activity against the NCI-60 cancer cell lines. Read More

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Synthesis of novel sulfonamides with anti-Alzheimer and antioxidant capacities.

Arch Pharm (Weinheim) 2021 Mar 22:e2000496. Epub 2021 Mar 22.

Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey.

A series of novel dopamine analogs incorporating urea and sulfonamide functional groups was synthesized from 3,4-dimethoxyphenethylamine. The reaction of 3,4-dimethoxyphenethylamine with N,N-dimethylcarbamoyl chloride, followed by the sulfonyl chlorination of the urea derivative, gave benzene-1-sulfonyl chloride 9, which was reacted with NH (aq) or N-alkyl amines to give related sulfonamides. The O-demethylation reaction of the subsequent compounds with BBr afforded four novel phenolic dopamine analogs including sulfonamide and urea in the same structure. Read More

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Piperazine and piperidine-substituted 7-hydroxy coumarins for the development of anti-inflammatory agents.

Arch Pharm (Weinheim) 2021 Mar 22:e2000354. Epub 2021 Mar 22.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.

Coumarins (2H-1-benzopyran-2-one), derivatives that can be isolated from several plants, have been reported for their anticoagulant, antimicrobial, anti-inflammatory, or anticancer activity. Some of these structures are currently approved for the treatment of cardiovascular diseases, as antibiotics or as an anticancer drug. Given the great potential of this structure and the limited number of studies that focus on molecules derived from carbon 8 of the benzopyranone heterocycle, we synthesized in this project 38 coumarin derivatives by substituting carbon 8 of the benzopyran ring with some aromatic and aliphatically substituted piperidines and piperazines. Read More

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Synthesis of 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their protective activity against oxidative stress.

Arch Pharm (Weinheim) 2021 Mar 18:e2100001. Epub 2021 Mar 18.

Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania.

A small library of 2-[(1H-indol-3-yl)methyl]-5-(alkylthio)-1,3,4-oxadiazoles was prepared, starting from indole-3-acetic acid methyl ester and its 5-methyl-substituted derivative. The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones. The latter were then S-alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. Read More

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Multitarget-directed therapeutics: (Urea/thiourea) derivatives of diverse heterocyclic-Lys conjugates.

Arch Pharm (Weinheim) 2021 Mar 17:e2000468. Epub 2021 Mar 17.

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, Karnataka, India.

The synthesis of a new small library of molecules containing bis-urea/thiourea pendants in lysine conjugated to three different heterocycles is described. The heterocycles used in this study have benzisoxazole/piperazine/piperidine units. After a detailed antimicrobial, antioxidant, and anti-inflammatory evaluation, it was found that the most active compounds are 10, 11, 14, 15, 18, 19 and 10, 11, 19 and 8, 9, 12, 13, 16, 17, respectively. Read More

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Synthesis of 2-(N-cyclicamino)quinoline combined with methyl (E)-3-(2/3/4-aminophenyl)acrylates as potential antiparasitic agents.

Arch Pharm (Weinheim) 2021 Mar 12:e2000331. Epub 2021 Mar 12.

Department of Chemistry, Faculty of Science, Rhodes University, Makhanda, South Africa.

A rationally designed series of 2-(N-cyclicamino)quinolines coupled with methyl (E)-3-(2/3/4-aminophenyl)acrylates was synthesized and subjected to in vitro screening bioassays for potential antiplasmodial and antitrypanosomal activities against a chloroquine-sensitive (3D7) strain of Plasmodium falciparum and nagana Trypanosoma brucei brucei 427, respectively. Substituent effects on activity were evaluated; meta-acrylate 24 and the ortho-acrylate 29 exhibited the highest antiplasmodial (IC  = 1.4 µM) and antitrypanosomal (IC  = 10. Read More

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Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators.

Arch Pharm (Weinheim) 2021 Mar 8:e2000458. Epub 2021 Mar 8.

Department of Medicinal Chemistry, Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, China.

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinone derivatives is reported as AMPKɑ1β1γ1 activators. The in vitro biological assay demonstrated that compounds 12k (EC [AMPKα1γ1β1] = 180 nM) and 13q (EC [AMPKα1γ1β1] = 2 nM) displayed significant enzyme activation. Read More

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Synthesis and docking calculations of tetrafluoronaphthalene derivatives and their inhibition profiles against some metabolic enzymes.

Arch Pharm (Weinheim) 2021 Mar 5:e2000409. Epub 2021 Mar 5.

Chemistry Department, Science Faculty, Sivas Cumhuriyet University, Sivas, Turkey.

Syntheses of tetrahydroepoxy, O-allylic, O-prenylic, and O-propargylic tetrafluoronaphthalene derivatives, starting from 1-bromo-2,3,4,5,6-pentafluorobenzene, are reported here for the first time. The O-substituted tetrafluoronaphthalene derivatives were designed and also synthesized via a one-pot nucleophilic substitution reaction in excellent yields, whereas the tetrafluorotetrahydroepoxynaphthalene derivate was synthesized via a reduction reaction in excellent yield. The chemical structures of all the synthesized molecules were characterized by nuclear magnetic resonance, infrared spectroscopy, and high-resolution mass spectrometry techniques. Read More

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Synthesis and antimalarial and anticancer evaluation of 7-chlorquinoline-4-thiazoleacetic derivatives containing aryl hydrazide moieties.

Arch Pharm (Weinheim) 2021 Mar 4:e2100002. Epub 2021 Mar 4.

Organic Synthesis Laboratory, Faculty of Pharmacy, Central University of Venezuela, Caracas, Venezuela.

Twelve 7-chloroquinoline derivatives were designed and synthesized using the principle of molecular hybridization through the coupling of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]acetic acid 1 with various benzoyl hydrazines 2a-l. The synthetic compounds were tested as antimalarials. Some of them showed an efficient in vitro activity as inhibitors of β-hematin formation and an in vivo activity in a murine model, resulting in compounds 8 and 9 as the most active ones with IC values of 0. Read More

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Design, synthesis, antibacterial evaluation, and computational studies of hybrid oxothiazolidin-1,2,4-triazole scaffolds.

Arch Pharm (Weinheim) 2021 Mar 3:e2000473. Epub 2021 Mar 3.

Bioorganic and Medicinal Chemistry Research Laboratory, Department of Pharmaceutical Sciences, Sam Higginbottom University of Agriculture, Technology & Sciences, Prayagraj, Uttar Pradesh, India.

Bacterial infections are a serious threat to human health due to the development of resistance against the presently used antibiotics. The problem of growing and widespread antibiotic resistance is only getting worse with the shortage of new classes of antibiotics, creating a substantial unmet medical need in the treatment of serious bacterial infections. Therefore, in the present work, we report 18 novel hybrid thiazolidine-1,2,4-triazole derivatives as DNA gyrase inhibitors. Read More

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Synthesis and antitumor potential of new arylidene ursolic acid derivatives via caspase-8 activation.

Arch Pharm (Weinheim) 2021 Mar 1:e2000448. Epub 2021 Mar 1.

School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou, China.

Continuing our studies on NO-donating ursolic acid-benzylidene derivatives as potential antitumor agents, we designed and synthesized a series of new arylidene derivatives containing NO-donating ursolic acid and aromatic heterocyclic units. Compounds 5c and 6c showed a significant broad-spectrum antitumor activity. Compound 5c exhibited nearly three- to nine-fold higher cytotoxicity as compared with the parent drug in A549, MCF-7, HepG-2, HT-29, and HeLa cells, and it was also found to be the most potent apoptosis inducer of MCF-7 cells. Read More

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Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives.

Arch Pharm (Weinheim) 2021 Feb 14;354(2):e2000199. Epub 2020 Oct 14.

Department of Chemistry, Perm State University, Perm, Russia.

Seventeen 1,4-benzoxazin-2-ones bearing the enaminone moiety and three of their analogs were tested for the antibacterial activity against Mycobacterium tuberculosis (H37Rv). Minimal bactericidal concentrations (MBCs) were determined after 41 days of incubation by BACTEC. 1,4-Benzoxazin-2-ones bearing the unsubstituted benzo moiety showed the most promising activities (MBC = 5. Read More

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February 2021

Synthesis, in silico, and in vitro studies of novel dopamine D and D receptor ligands.

Arch Pharm (Weinheim) 2021 Feb 22:e2000486. Epub 2021 Feb 22.

Institute of Pharmaceutical and Medicinal Chemistry, Heinrich Heine University Düsseldorf, Universitaetsstr. 1, Duesseldorf, NRW, Germany.

Dopamine is an important neurotransmitter in the human brain and its altered concentrations can lead to various neurological diseases. We studied the binding of novel compounds at the dopamine D (D R) and D (D R) receptor subtypes, which belong to the D -like receptor family. The synthesis, in silico, and in vitro characterization of 10 dopamine receptor ligands were performed. Read More

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February 2021

(+)-Camphor and (-)-borneol derivatives as potential anti-orthopoxvirus agents.

Arch Pharm (Weinheim) 2021 Feb 19:e2100038. Epub 2021 Feb 19.

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch Russian Academy of Sciences, Novosibirsk, Russian Federation.

Although the World Health Organisation had announced that smallpox was eradicated over 40 years ago, the disease and other related pathogenic poxviruses such as monkeypox remain potential bioterrorist weapons and could also re-emerge as natural infections. We have previously reported (+)-camphor and (-)-borneol derivatives with an antiviral activity against the vaccinia virus. This virus is similar to the variola virus (VARV), the causative agent of smallpox, but can be studied at BSL-2 facilities. Read More

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February 2021