Publication: Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents
Issued Date
2011-02-01
Resource Type
ISSN
17683254
02235234
02235234
Other identifier(s)
2-s2.0-79151482944
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
European Journal of Medicinal Chemistry. Vol.46, No.2 (2011), 738-742
Suggested Citation
Supaluk Prachayasittikul, Apilak Worachartcheewan, Chanin Nantasenamat, Maneekarn Chinworrungsee, Nirun Sornsongkhram, Somsak Ruchirawat, Virapong Prachayasittikul Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents. European Journal of Medicinal Chemistry. Vol.46, No.2 (2011), 738-742. doi:10.1016/j.ejmech.2010.12.009 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/11731
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents
Other Contributor(s)
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.