Publication:
Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents

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Issued Date

2011

Resource Type

Article

File Type

application/pdf

ISSN

2235234

DOI

10.1016/j.ejmech.2010.12.009

Other identifier(s)

2-s2.0-79151482944

Rights Holder(s)

มหาวิทยาลัยศรีนครินทรวิโรฒ

Bibliographic Citation

European Journal of Medicinal Chemistry. Vol 46, No.2 (2011), p.738-742

Suggested Citation

Prachayasittikul S., Worachartcheewan A., Nantasenamat C., Chinworrungsee M., Sornsongkhram N., Ruchirawat S., Prachayasittikul V. 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), p.738-742. doi:10.1016/j.ejmech.2010.12.009 Retrieved from: https://hdl.handle.net/20.500.14740/7390

Title

Synthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents

Author(s)

Prachayasittikul S.
 Worachartcheewan A.
 Nantasenamat C.
 Chinworrungsee M.
 Sornsongkhram N.
 Ruchirawat S.
 Prachayasittikul V.

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.

Subject(s)

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

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URI

https://hdl.handle.net/20.500.14740/7390

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Scopus: Year 1983-2021

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