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

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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.date.issuedBE2554
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.format.mimetypeapplication/pdf
dc.identifier.citationEuropean Journal of Medicinal Chemistry. Vol 46, No.2 (2011), p.738-742
dc.identifier.doi10.1016/j.ejmech.2010.12.009
dc.identifier.issn2235234
dc.identifier.other2-s2.0-79151482944
dc.identifier.urihttps://hdl.handle.net/20.500.14740/7390
dc.rights.holderมหาวิทยาลัยศรีนครินทรวิโรฒ
dc.subject.other2 (1 adamantylthio)pyrimidin 4(3h) one
dc.subject.other2 (1 butylthio)pyrimidin 4(3h) one
dc.subject.other2 (2 butylthio)pyrimidin 4(3h) one
dc.subject.other2 (benzylthio)pyrimidin 4(3h) one
dc.subject.other2 (cyclohexylmethylthio)pyrimidin 4(3h) one
dc.subject.other2 thiopyrimidine 4 one
dc.subject.otherAmpicillin
dc.subject.otherAntiinfective agent
dc.subject.otherAntineoplastic agent
dc.subject.otherBromine derivative
dc.subject.otherEtoposide
dc.subject.otherPyrimidine derivative
dc.subject.otherThiouracil
dc.subject.otherUnclassified drug
dc.subject.otherAeromonas hydrophila
dc.subject.otherAlkylation
dc.subject.otherAntibacterial activity
dc.subject.otherAntifungal activity
dc.subject.otherAntimalarial activity
dc.subject.otherAntimicrobial activity
dc.subject.otherAntineoplastic activity
dc.subject.otherArticle
dc.subject.otherBacillus cereus
dc.subject.otherBacillus subtilis
dc.subject.otherCancer resistance
dc.subject.otherCandida albicans
dc.subject.otherCitrobacter freundii
dc.subject.otherControlled study
dc.subject.otherCorynebacterium diphtheriae
dc.subject.otherCytotoxicity
dc.subject.otherDrug activity
dc.subject.otherDrug synthesis
dc.subject.otherEdwardsiella tarda
dc.subject.otherEnterococcus faecalis
dc.subject.otherEscherichia coli
dc.subject.otherHuman
dc.subject.otherHuman cell
dc.subject.otherKlebsiella pneumoniae
dc.subject.otherListeria monocytogenes
dc.subject.otherLung small cell cancer
dc.subject.otherMicrococcus luteus
dc.subject.otherMoraxella catarrhalis
dc.subject.otherMorganella morganii
dc.subject.otherNeisseria mucosa
dc.subject.otherNonhuman
dc.subject.otherPlasmodium falciparum
dc.subject.otherPlesiomonas shigelloides
dc.subject.otherPseudomonas aeruginosa
dc.subject.otherSalmonella choleraesuis
dc.subject.otherSalmonella typhimurium
dc.subject.otherShigella dysenteriae
dc.subject.otherStaphylococcus aureus
dc.subject.otherStaphylococcus epidermidis
dc.subject.otherStenotrophomonas maltophilia
dc.subject.otherStreptococcus pyogenes
dc.subject.otherStructure activity relation
dc.subject.otherVibrio cholerae
dc.subject.otherVibrio mimicus
dc.subject.otherYeast
dc.subject.otherAnimals
dc.subject.otherAnti-Bacterial Agents
dc.subject.otherAntifungal Agents
dc.subject.otherAntimalarials
dc.subject.otherAntineoplastic Agents
dc.subject.otherCandida albicans
dc.subject.otherCell Line, Tumor
dc.subject.otherCell Proliferation
dc.subject.otherDose-Response Relationship, Drug
dc.subject.otherDrug Screening Assays, Antitumor
dc.subject.otherHumans
dc.subject.otherMice
dc.subject.otherMicrobial Sensitivity Tests
dc.subject.otherMolecular Structure
dc.subject.otherMoraxella (Branhamella) catarrhalis
dc.subject.otherParasitic Sensitivity Tests
dc.subject.otherPlasmodium falciparum
dc.subject.otherPyrimidinones
dc.subject.otherStereoisomerism
dc.subject.otherStreptococcus pyogenes
dc.subject.otherStructure-Activity Relationship
dc.titleSynthesis and structure-activity relationship of 2-thiopyrimidine-4-one analogs as antimicrobial and anticancer agents
dc.typeArticle
dspace.entity.typePublication
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