Synthesis of pyrrolo[3,2-c]carbazole-2-carbohydrazides and pyrrolo[3,2-c]carbazol-2-yl-1,3,4-oxadiazoles and their in vitro antibacterial evaluation

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dc.authorscopusid57201682024
dc.authorscopusid57190258762
dc.authorscopusid57226748981
dc.authorscopusid55326408200
dc.authorscopusid55308985300
dc.contributor.authorSağlam, Mehmet Turgut
dc.contributor.authorGündogdu, Aycan
dc.contributor.authorHora, Mehmet
dc.contributor.authorKandemir, Hakan
dc.contributor.authorŞengül, İbrahim Fazıl
dc.date.accessioned2022-05-11T14:04:40Z
dc.date.available2022-05-11T14:04:40Z
dc.date.issued2021
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractA number of novel pyrrolo[3,2-c]carbazole-2-carbohydrazides 5a–d was prepared from readily available 6-methyl-1,6-dihydropyrrolo[3,2-c]carbazole-2-carboxylate 3 and underwent cyclodehydration to produce the corresponding 2-(6-ethyl-1,6-dihydropyrrolo[3,2-c]carbazol-2-yl)-1,3,4-oxadiazoles 6a–d with p-toluenesulfonyl chloride (p-TsCl) and N,N-diisopropylethylamine (DIPEA) as dehydrative reagents. The structures of the targeted compounds were confirmed through 1H NMR, 13C NMR, IR, mass spectrometry and single crystal X-ray diffraction techniques. Moreover, the antibacterial properties of the synthesized compounds were evaluated against colistin resistant (ColR) Klebsiella pneumoniae, ColR Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli and Staphylococcus aureus. Among the synthesized compounds, 5d was found to be active on ColR K. pneumoniae (MIC = 64 µg/mL) while compounds 4 (MIC= <64 µg/mL) and 6a (MIC==<64 µg/mL) were active on E. coli. Preliminary assay showed that the pyrrolo[3,2-c]carbazole-2-carbohydrazides and 2-(6-methyl-1,6-dihydropyrrolo[3,2-c]carbazol-2-yl)-1,3,4-oxadiazoles showed promising antibacterial activity on important nosocomial multi drug resistant (MDR) pathogens. © 2021 Taylor & Francis Group, LLC.
dc.description.sponsorshipTürkiye Bilimsel ve Teknolojik Araştirma Kurumu, TÜBITAK: 120Z069
dc.description.sponsorshipThis work has been supported by The Scientific and Technological Research Council of Turkey [Project Number: 120Z069].
dc.identifier.doi10.1080/00397911.2021.1966040
dc.identifier.endpage3174
dc.identifier.issn0039-7911
dc.identifier.issue20en_US
dc.identifier.scopus2-s2.0-85112537530
dc.identifier.scopusqualityQ3
dc.identifier.startpage3164
dc.identifier.urihttps://doi.org/10.1080/00397911.2021.1966040
dc.identifier.urihttps://hdl.handle.net/20.500.11776/4703
dc.identifier.volume51
dc.identifier.wosWOS:000685025000001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorKandemir, Hakan
dc.language.isoen
dc.publisherTaylor and Francis Ltd.
dc.relation.ispartofSynthetic Communications
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject1,3,4-oxadiazole
dc.subjectcolistin
dc.subjectMDR pathogens
dc.subjectPyrrolo-carbazole
dc.subject2 (6 ethyl 1,6 dihydropyrrolo[3,2 c]carbazol 2 yl) 1,3,4 oxadiazole derivative
dc.subjectantiinfective agent
dc.subjectcolistin
dc.subjectethylamine
dc.subjectn,n diisopropylethylamine
dc.subjectpyrrolo[3,2 c]carbazol 2 yl 1,3,4 oxadiazole derivative
dc.subjectpyrrolo[3,2 c]carbazole 2 carbohydrazide derivative
dc.subjecttoluene derivative
dc.subjectunclassified drug
dc.subjectAcinetobacter baumannii
dc.subjectantibacterial activity
dc.subjectArticle
dc.subjectcarbon nuclear magnetic resonance
dc.subjectcolistin resistance
dc.subjectcontrolled study
dc.subjectdrug structure
dc.subjectdrug synthesis
dc.subjectEscherichia coli
dc.subjectin vitro study
dc.subjectinfrared radiation
dc.subjectKlebsiella pneumoniae
dc.subjectmass spectrometry
dc.subjectminimum inhibitory concentration
dc.subjectnonhuman
dc.subjectproton nuclear magnetic resonance
dc.subjectPseudomonas aeruginosa
dc.subjectStaphylococcus aureus
dc.subjectX ray diffraction
dc.titleSynthesis of pyrrolo[3,2-c]carbazole-2-carbohydrazides and pyrrolo[3,2-c]carbazol-2-yl-1,3,4-oxadiazoles and their in vitro antibacterial evaluation
dc.typeArticle

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