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Synthesis and biological evaluation of (S)-4-aminoquinazoline alcohols

ArticleAçık Erişim

Özet

A simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia coli WP2uvrA tester strains at 0.01, 0.1, and 1 μg/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1 μg/plate dose. © 2010 Elsevier Ltd. All rights reserved.

Anahtar Kelimeler

antimutagenic agentquinazoline derivativearticlechemical modificationchlorinationdrug synthesisEscherichia coligenotoxicitymutagenicitynonhumanpriority journalSalmonella typhimurium
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorCakici, Murat
dc.contributor.authorCatir, Mustafa
dc.contributor.authorKarabuga, Semistan
dc.contributor.authorKilic, Hamdullah
dc.contributor.authorUlukanli, Sabri
dc.contributor.authorGulluce, Medine
dc.contributor.authorOrhan, Furkan
dc.date.accessioned2026-10-18T20:30:51.258299959Z
dc.date.available2026-10-18T20:30:51.258299959Z
dc.date.issued2010
dc.description.abstractA simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia coli WP2uvrA tester strains at 0.01, 0.1, and 1 μg/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1 μg/plate dose. © 2010 Elsevier Ltd. All rights reserved.
dc.description.sponsorshipThe financial support from the Scientific and Technological Research Council of Turkey (TUBITAK) ( TBAG-108T116 ) is gratefully acknowledged. In addition, the authors would like to thank Dr. Graham Eaton from the Leicester University for the HRMS measurements.
dc.identifier.doi10.1016/j.tetasy.2010.05.040
dc.identifier.endpage2031
dc.identifier.issn1362-511X
dc.identifier.issue16
dc.identifier.scopus2-s2.0-77956230396
dc.identifier.startpage2027
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/ebyu/16013
dc.identifier.volume21
dc.identifier.wosWOS:000281977500013
dc.language.isoen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartofTetrahedron Asymmetry
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectantimutagenic agent
dc.subjectquinazoline derivative
dc.subjectarticle
dc.subjectchemical modification
dc.subjectchlorination
dc.subjectdrug synthesis
dc.subjectEscherichia coli
dc.subjectgenotoxicity
dc.subjectmutagenicity
dc.subjectnonhuman
dc.subjectpriority journal
dc.subjectSalmonella typhimurium
dc.titleSynthesis and biological evaluation of (S)-4-aminoquinazoline alcohols
dc.typeArticle
dspace.entity.typePublication
rdl.citation.scopus20
rdl.citation.wos18
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)
rdl.wos.indexIndex Chemicus (IC)