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Please use this identifier to cite or link to this item: https://ir.swu.ac.th/jspui/handle/123456789/14570
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dc.contributor.authorPrachayasittikul S.
dc.contributor.authorWorachartcheewan A.
dc.contributor.authorNantasenamat C.
dc.contributor.authorChinworrungsee M.
dc.contributor.authorSornsongkhram N.
dc.contributor.authorRuchirawat S.
dc.contributor.authorPrachayasittikul V.
dc.date.accessioned2021-04-05T03:35:38Z-
dc.date.available2021-04-05T03:35:38Z-
dc.date.issued2011
dc.identifier.issn2235234
dc.identifier.other2-s2.0-79151482944
dc.identifier.urihttps://ir.swu.ac.th/jspui/handle/123456789/14570-
dc.identifier.urihttps://www.scopus.com/inward/record.uri?eid=2-s2.0-79151482944&doi=10.1016%2fj.ejmech.2010.12.009&partnerID=40&md5=2174a7714d042ee5e89f1cfb500ed788
dc.description.abstractConsidering 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.
dc.subject2 (1 adamantylthio)pyrimidin 4(3h) one
dc.subject2 (1 butylthio)pyrimidin 4(3h) one
dc.subject2 (2 butylthio)pyrimidin 4(3h) one
dc.subject2 (benzylthio)pyrimidin 4(3h) one
dc.subject2 (cyclohexylmethylthio)pyrimidin 4(3h) one
dc.subject2 thiopyrimidine 4 one
dc.subjectampicillin
dc.subjectantiinfective agent
dc.subjectantineoplastic agent
dc.subjectbromine derivative
dc.subjectetoposide
dc.subjectpyrimidine derivative
dc.subjectthiouracil
dc.subjectunclassified drug
dc.subjectAeromonas hydrophila
dc.subjectalkylation
dc.subjectantibacterial activity
dc.subjectantifungal activity
dc.subjectantimalarial activity
dc.subjectantimicrobial activity
dc.subjectantineoplastic activity
dc.subjectarticle
dc.subjectBacillus cereus
dc.subjectBacillus subtilis
dc.subjectcancer resistance
dc.subjectCandida albicans
dc.subjectCitrobacter freundii
dc.subjectcontrolled study
dc.subjectCorynebacterium diphtheriae
dc.subjectcytotoxicity
dc.subjectdrug activity
dc.subjectdrug synthesis
dc.subjectEdwardsiella tarda
dc.subjectEnterococcus faecalis
dc.subjectEscherichia coli
dc.subjecthuman
dc.subjecthuman cell
dc.subjectKlebsiella pneumoniae
dc.subjectListeria monocytogenes
dc.subjectlung small cell cancer
dc.subjectMicrococcus luteus
dc.subjectMoraxella catarrhalis
dc.subjectMorganella morganii
dc.subjectNeisseria mucosa
dc.subjectnonhuman
dc.subjectPlasmodium falciparum
dc.subjectPlesiomonas shigelloides
dc.subjectPseudomonas aeruginosa
dc.subjectSalmonella choleraesuis
dc.subjectSalmonella typhimurium
dc.subjectShigella dysenteriae
dc.subjectStaphylococcus aureus
dc.subjectStaphylococcus epidermidis
dc.subjectStenotrophomonas maltophilia
dc.subjectStreptococcus pyogenes
dc.subjectstructure activity relation
dc.subjectVibrio cholerae
dc.subjectVibrio mimicus
dc.subjectyeast
dc.subjectAnimals
dc.subjectAnti-Bacterial Agents
dc.subjectAntifungal Agents
dc.subjectAntimalarials
dc.subjectAntineoplastic Agents
dc.subjectCandida albicans
dc.subjectCell Line, Tumor
dc.subjectCell Proliferation
dc.subjectDose-Response Relationship, Drug
dc.subjectDrug Screening Assays, Antitumor
dc.subjectHumans
dc.subjectMice
dc.subjectMicrobial Sensitivity Tests
dc.subjectMolecular Structure
dc.subjectMoraxella (Branhamella) catarrhalis
dc.subjectParasitic Sensitivity Tests
dc.subjectPlasmodium falciparum
dc.subjectPyrimidinones
dc.subjectStereoisomerism
dc.subjectStreptococcus pyogenes
dc.subjectStructure-Activity Relationship
dc.titleSynthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents
dc.typeArticle
dc.rights.holderScopus
dc.identifier.bibliograpycitationEuropean Journal of Medicinal Chemistry. Vol 46, No.2 (2011), p.738-742
dc.identifier.doi10.1016/j.ejmech.2010.12.009
Appears in Collections:Scopus 1983-2021

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