Novel microwave assisted synthesis and antimicrobial activity of new quinolone-hybrids

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dc.authorid0000-0002-8444-2011en_US
dc.contributor.authorCeylan, Şule
dc.contributor.authorBayrak, Hacer
dc.contributor.authorÖzdemir, Serap Başoğlu
dc.contributor.authorUygun, Yıldız
dc.contributor.authorMermer, Arif
dc.contributor.authorDemirbaş, Neslihan
dc.contributor.authorÜlker, Serdar
dc.date.accessioned2021-09-14T11:13:16Z
dc.date.available2021-09-14T11:13:16Z
dc.date.issued2016
dc.departmentAÇÜ, Orman Fakültesi, Orman Endüstri Mühendisliği Bölümüen_US
dc.description.abstractBackground: Carbo(thio)amid derivatives 4a, 4b were obtained starting from nalidixic acid in three steps. The acidic treatment of compound 4a generated the corresponding 1,3,4-oxadiazole (5), while the compound 4a gave 1,2,4-triazole derivatives 8a, 8b in basic media. The condensation of 4a with ethyl bromoacetate and 4-chlorophenacyl bromide afforded 1,3-oxazolidine, 6 and 1,3-thiazolidine, 7 derivatives. The synthesis of Mannich bases of 9-15 and 17-19 were achieved from the reaction of 1,2,4-triazoles, 8a, 8b and 1,3,4-oxadiazole, 16, with several heterocyclic amines that has biological activity. Methods: In this article, a series of triazole or 1,3,4-oxadiazole rings containing some novel biologically active quinolone derivatives. Conventional and microwave assisted methods were used for all syntheses. Moreover, the effect of acid catalyst on Mannich reactions was investigated. The structures of newly synthesized compounds were elucidated on the basis of H-1 NMR, C-13 NMR, FT IR, EI MS techniques and elemental analysis. All these compounds were screened in vitro for their antimicrobial activity against various gram-positive and gram-negative bacterial and fungal strains. Results: This study reports the successful synthesis of some new hybrid compounds starting from nalidixic acid. Two methods containing conventional and microwave assistance with/without catalyst were used to obtain the target compounds. Microwave assistance supplied more efficient way leading the formation of target compounds. Moreover, the effect of acid catalyst on Mannich reactions was investigated. The antimicrobial activity screening studies were also performed in the study. Conclusion: The antimicrobial screening suggests that the compounds containing norfloxacin (9a,b and 17), ciprofloxacin (10a,b and 18) or 7-aminocephalosporanic (12) acid nucleus displayed excellent antimicrobial activity. Moreover, some of them (5-7, 8-13, 15-18) displayed inhibition properties on Escherichia coli (Ec) and Mycobacterium smegmatis (Ms) better from ampicillin or streptomycin with the mic value 0.24 mu g/mL.
dc.identifier.citationCeylan, S., Bayrak, H., Özdemir, S. B., Uygun, Y., Mermer, A., Demirbaş, N., & Ülker, S. (2016). Novel microwave assisted synthesis and antimicrobial activity of new quinolone-hybrids. Letters in Organic Chemistry, 13(9), 636-651.en_US
dc.identifier.doi10.2174/1570178613666160927125221
dc.identifier.endpage651en_US
dc.identifier.issue9en_US
dc.identifier.scopusqualityQ4
dc.identifier.startpage636en_US
dc.identifier.urihttps://hdl.handle.net/11494/3426
dc.identifier.volume13en_US
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorCeylan, Şule
dc.language.isoenen_US
dc.publisherBentham Science Publ Ltden_US
dc.relation.ispartofLetters in Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.relation.tubitak113Z181
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectNalidixic aciden_US
dc.subject1,2,4-triazoleen_US
dc.subject1,3,4-oxadiazoleen_US
dc.subjectNorfloxacinen_US
dc.subjectCiprofloxacinen_US
dc.subjectMannich baseen_US
dc.subjectAntimicrobial activityen_US
dc.subjectMicrowaveen_US
dc.titleNovel microwave assisted synthesis and antimicrobial activity of new quinolone-hybridsen_US
dc.typeArticle

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