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https://ir.swu.ac.th/jspui/handle/123456789/14570| Title: | Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents |
| Authors: | Prachayasittikul S. Worachartcheewan A. Nantasenamat C. Chinworrungsee M. Sornsongkhram N. Ruchirawat S. Prachayasittikul V. |
| Keywords: | 2 (1 adamantylthio)pyrimidin 4(3h) one 2 (1 butylthio)pyrimidin 4(3h) one 2 (2 butylthio)pyrimidin 4(3h) one 2 (benzylthio)pyrimidin 4(3h) one 2 (cyclohexylmethylthio)pyrimidin 4(3h) one 2 thiopyrimidine 4 one ampicillin antiinfective agent antineoplastic agent bromine derivative etoposide pyrimidine derivative thiouracil unclassified drug Aeromonas hydrophila alkylation antibacterial activity antifungal activity antimalarial activity antimicrobial activity antineoplastic activity article Bacillus cereus Bacillus subtilis cancer resistance Candida albicans Citrobacter freundii controlled study Corynebacterium diphtheriae cytotoxicity drug activity drug synthesis Edwardsiella tarda Enterococcus faecalis Escherichia coli human human cell Klebsiella pneumoniae Listeria monocytogenes lung small cell cancer Micrococcus luteus Moraxella catarrhalis Morganella morganii Neisseria mucosa nonhuman Plasmodium falciparum Plesiomonas shigelloides Pseudomonas aeruginosa Salmonella choleraesuis Salmonella typhimurium Shigella dysenteriae Staphylococcus aureus Staphylococcus epidermidis Stenotrophomonas maltophilia Streptococcus pyogenes structure activity relation Vibrio cholerae Vibrio mimicus yeast Animals Anti-Bacterial Agents Antifungal Agents Antimalarials Antineoplastic Agents Candida albicans Cell Line, Tumor Cell Proliferation Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Humans Mice Microbial Sensitivity Tests Molecular Structure Moraxella (Branhamella) catarrhalis Parasitic Sensitivity Tests Plasmodium falciparum Pyrimidinones Stereoisomerism Streptococcus pyogenes Structure-Activity Relationship |
| Issue Date: | 2011 |
| Abstract: | Considering that some thiopyrimidines were previously reported as potential therapeutics, the present study achieved novel analogs of bioactive 2-substituted thiopyrimidines-4-(3H)-ones via base catalyzed alkylation reaction of 2-thiouracil using alkyl and aralkyl bromides. The title compounds were 2-(1-butylthio)pyrimidine-4(3H)-one (5a), 2-(2-butylthio)pyrimidine-4(3H)-one (5b), 2-(cyclohexylmethylthio)pyrimidine-4(3H)-one (5c), 2-(benzylthio) pyrimidine-4(3H)-one (5d) and 2-(1-adamantylthio)pyrimidine-4(3H)-one (5e). Bioactivity tests revealed that thiopyrimidines 5a, 5c, 5d and 5e exhibited antimicrobial activity. The thiopyrimidine-4-one (5c) showed complete inhibition against Streptococcus pyogenes and Branhamella catarrhalis as well as antifungal action against Candida albicans. Significantly, the 1-adamantylthiopyrimidine (5e) was shown to be the most potent cytotoxic compound against multidrug-resistant small cell lung cancer (H69AR). Their structure-activity relationships were discussed. © 2010 Elsevier Masson SAS. All rights reserved. |
| URI: | https://ir.swu.ac.th/jspui/handle/123456789/14570 https://www.scopus.com/inward/record.uri?eid=2-s2.0-79151482944&doi=10.1016%2fj.ejmech.2010.12.009&partnerID=40&md5=2174a7714d042ee5e89f1cfb500ed788 |
| ISSN: | 2235234 |
| Appears in Collections: | Scopus 1983-2021 |
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