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Syntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents

ArticleAçık Erişim

Özet

Four multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9) and 4-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9a). Compound 9 was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions. The best antituberculosis activity was exhibited by 2-isopropylphenanthrene-3-ol (11). © 2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

Anahtar Kelimeler

antituberculosismiltironeMulticaulinsynthesisAntitubercular AgentsDose-Response Relationship, DrugMicrobial Sensitivity TestsMolecular StructureMycobacteriumPhenanthrenesStructure-Activity Relationship2 isopropyl 3 methoxy 9,10 dihydrophenanthrene2 isopropyl 3 methoxyphenanthrene2 isopropylphenanthren 3 ol2 isopropylphenanthren 3,4 dione4 isopropyl 3 methoxy 9,10 dihydrophenanthrenephenanthrene derivativestreptomycintuberculostatic agentunclassified drugphenanthreneantibacterial activityArticlechemical reactioncontrolled studydrug screeningdrug synthesisin vitro studyminimum inhibitory concentrationMycobacterium bovis
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorBurmaoğlu, Serdar
dc.contributor.authorSeçinti, Hatice
dc.contributor.authorMozioğlu, Erkan
dc.contributor.authorGören, Ahmet C.
dc.contributor.authorAltundaş, Ramazan
dc.contributor.authorSeçen, Hasan
dc.date.accessioned2026-10-18T20:29:32.456986284Z
dc.date.available2026-10-18T20:29:32.456986284Z
dc.date.issued2017
dc.description.abstractFour multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9) and 4-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9a). Compound 9 was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions. The best antituberculosis activity was exhibited by 2-isopropylphenanthrene-3-ol (11). © 2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.
dc.description.sponsorshipWe thank The Scientific and Technological Research Council of Turkey (Tubitak, grant number: 108T115) for financial support.
dc.identifier.doi10.1080/14756366.2017.1337758
dc.identifier.eissn1475-6374
dc.identifier.endpage884
dc.identifier.issn1475-6366
dc.identifier.issue1
dc.identifier.pmcidPMC6445210
dc.identifier.pmid28661186
dc.identifier.scopus2-s2.0-85021645782
dc.identifier.startpage878
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/ebyu/14731
dc.identifier.volume32
dc.identifier.wosWOS:000427397900001
dc.language.isoen
dc.publisherTaylor and Francis Ltd
dc.relation.ispartofJournal of Enzyme Inhibition and Medicinal Chemistry
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectantituberculosis
dc.subjectmiltirone
dc.subjectMulticaulin
dc.subjectsynthesis
dc.subjectAntitubercular Agents
dc.subjectDose-Response Relationship, Drug
dc.subjectMicrobial Sensitivity Tests
dc.subjectMolecular Structure
dc.subjectMycobacterium
dc.subjectPhenanthrenes
dc.subjectStructure-Activity Relationship
dc.subject2 isopropyl 3 methoxy 9,10 dihydrophenanthrene
dc.subject2 isopropyl 3 methoxyphenanthrene
dc.subject2 isopropylphenanthren 3 ol
dc.subject2 isopropylphenanthren 3,4 dione
dc.subject4 isopropyl 3 methoxy 9,10 dihydrophenanthrene
dc.subjectphenanthrene derivative
dc.subjectstreptomycin
dc.subjecttuberculostatic agent
dc.subjectunclassified drug
dc.subjectphenanthrene
dc.subjectantibacterial activity
dc.subjectArticle
dc.subjectchemical reaction
dc.subjectcontrolled study
dc.subjectdrug screening
dc.subjectdrug synthesis
dc.subjectin vitro study
dc.subjectminimum inhibitory concentration
dc.subjectMycobacterium bovis
dc.titleSyntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents
dc.typeArticle
dspace.entity.typePublication
rdl.citation.scopus6
rdl.citation.wos6
rdl.departmentb Tercan Vocational High School , Erzincan University , Erzincan , Turkey.
rdl.oa.statusgold
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.source.indexPUBMED
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)
rdl.wos.indexIndex Chemicus (IC)