Microwave-assisted synthesis of novel mannich base and conazole derivatives containing biologically active pharmacological groups

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dc.contributor.authorCebeci, Yıldız Uygun
dc.contributor.authorCeylan, Şule
dc.contributor.authorDemirbaş, Neslihan D.
dc.contributor.authorKaraoǧlu, Şeng̈ul Alpay
dc.date.accessioned2021-04-29T12:39:30Z
dc.date.available2021-04-29T12:39:30Z
dc.date.issued2021
dc.departmentAÇÜ, Orman Fakültesi, Orman Endüstri Mühendisliği Bölümüen_US
dc.description.abstractBackground: The aim of this study was to synthesize new Mannich bases and conazol derivatives with biological activity by the microwave-assisted method. Introduction: 1,2,4-Triazole-3-one (3) acquired from tryptamine was transformed to the corresponding carbox(thio)amides (6a-c) via several steps. Compounds 6a-c were refluxed with sodium hydroxide to yield 1,2,4-triazole derivatives (7a-c). Compounds 3 and 7a-c on treatment with different heterocyclic secondary amines in an ambiance with formaldehyde afforded the Mannich bases 8-15 having diverse pharmacophore units with biologically active sites. The reaction of compound 3 and 2-bromo-1-(4-chlorophenyl) ethanone in the presence of sodium ethoxide gave the corresponding product 2-substituted-1,2,4-triazole-3-one, 16, which was reduced to 1,2,4-triazoles (17). Synthesis of compounds 18, 19, and 20 was carried out starting from compounds 17 with 4-chlorobenzyl chloride (for 18), 2,4-dichlorobenzyl chloride (for 19), and 2,6-dichlorobenzyl chloride (for 20). Methods: The conventional technique was utilized for the synthesis of compounds, 3-7, and microwave-assisted technique for the compounds, 8-20. That is, green chemistry techniques were applied during these reactions. The structures of molecules were elucidated on the foundation of 1H NMR, 13C NMR, FT-IR, EI-MS methods, and elemental analysis. Novel synthesized molecules were investigated for their antimicrobial activity using MIC (minimum inhibitory concentration) method. Results: Aminoalkylation of triazole derivatives 3 and 7a-c with fluoroquinolones such as ciprofloxacin and norfloxacin provided an enhancement to the bioactivity of Mannich bases 8-11 against the tested microorganisms. The MIC values ranged between <0.24 and 3.9 ?g/mL. Moreover, molecules 10 and 11 exhibited more effects on M. smegmatis than the other compounds by the MIC values of <1 ?g/mL. They have shown very good antituberculosis activity. Conclusion: Most of the synthesized structures were observed to have excellent antimicrobial activity against most microorganisms taken into account. These molecules have better activity than the standard drug ampicillin and streptomycin.
dc.identifier.citationCebeci, Y. U., Ceylan, Ş., Demirbaş, N. D., Karaoğlu, Ş. A. (2021). Microwave-assisted synthesis of novel mannich base and conazole derivatives containing biologically active pharmacological groups, Letters in Drug Design and Discovery 18(3), 269-283en_US
dc.identifier.doi10.2174/1570180817999201016154034
dc.identifier.endpage283en_US
dc.identifier.issue3en_US
dc.identifier.scopusqualityQ3
dc.identifier.startpage269en_US
dc.identifier.urihttps://hdl.handle.net/11494/3183
dc.identifier.volume18en_US
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorCeylan, Şule
dc.language.isoenen_US
dc.publisherBentham Science Publishersen_US
dc.relation.ispartofLetters in Drug Design and Discovery
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.relation.tubitak113Z181
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject1, 2, 4-triazoleen_US
dc.subjectAntimicrobial activityen_US
dc.subjectConazoleen_US
dc.subjectMannichen_US
dc.subjectTryptamineen_US
dc.titleMicrowave-assisted synthesis of novel mannich base and conazole derivatives containing biologically active pharmacological groupsen_US
dc.typeArticle

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