Bioorganic & medicinal chemistry letters · 2021
Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition.
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Nesaragi Aravind R, Kamble Ravindra R, Bayannavar Praveen K, Shaikh Saba Kauser J, Hoolageri Swati R, Kodasi Barnabas, Joshi Shrinivas D, Kumbar Vijay M
Аннотация
Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones 8j-v were synthesized by click chemistry as an ultimate tactic where [3 + 2] cycloaddition of azides with terminal alkynes has been evolved. Herein, we are inclined to divulge the implication and prevalence of CuSO4·5H2O and THF/water promoted [3 + 2] cycloaddition reactions. The foremost supremacy of this method are transitory reaction times, facile workup, excellent yields (88-92%) with exorbitant purity and regioselective single product formation both under conventional and microwave method. Docking studies illustrated strong binding interactions with enzyme InhA-D148G (PDB ID: 4DQU) by means of high C-score values. The anti-tubercular and antifungal screening of synthesized compounds proclaimed promising activity. The in vitro and in silico studies imply that these triazoles appended quinolines may acquire the ideal structural prerequisites for auxiliary expansion of novel therapeutic agents.
Предметные рубрики MeSH
Antifungal AgentsAntitubercular AgentsAspergillusCandida albicansCatalysisCell SurvivalCopperCycloaddition ReactionDose-Response Relationship, DrugHEK293 CellsHumansMicrobial Sensitivity TestsMicrowavesMolecular StructureMycobacterium tuberculosisQuinolinesStereoisomerismStructure-Activity RelationshipTriazoles