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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
antiinfective agent
antineoplastic agent
bromine derivative
pyrimidine derivative
unclassified drug
Aeromonas hydrophila
antibacterial activity
antifungal activity
antimalarial activity
antimicrobial activity
antineoplastic activity
Bacillus cereus
Bacillus subtilis
cancer resistance
Candida albicans
Citrobacter freundii
controlled study
Corynebacterium diphtheriae
drug activity
drug synthesis
Edwardsiella tarda
Enterococcus faecalis
Escherichia coli
human cell
Klebsiella pneumoniae
Listeria monocytogenes
lung small cell cancer
Micrococcus luteus
Moraxella catarrhalis
Morganella morganii
Neisseria mucosa
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
Anti-Bacterial Agents
Antifungal Agents
Antineoplastic Agents
Candida albicans
Cell Line, Tumor
Cell Proliferation
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Microbial Sensitivity Tests
Molecular Structure
Moraxella (Branhamella) catarrhalis
Parasitic Sensitivity Tests
Plasmodium falciparum
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.
ISSN: 2235234
Appears in Collections:SCOPUS 1983-2021

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