Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition

被引:43
|
作者
Nesaragi, Aravind R. [1 ]
Kamble, Ravindra R. [1 ]
Bayannavar, Praveen K. [1 ]
Shaikh, Saba Kauser J. [1 ]
Hoolageri, Swati R. [1 ]
Kodasi, Barnabas [1 ]
Joshi, Shrinivas D. [2 ]
Kumbar, Vijay M. [3 ]
机构
[1] Karnatak Univ Dharwad, Dept Studies Chem, Dharwad 580003, Karnataka, India
[2] SETs Coll Pharm, Dept Pharmaceut Chem, Novel Drug Design & Discovery Lab, Dharwad 580002, Karnataka, India
[3] Maratha Mandals NGH Inst, Cent Res Lab, Dent Sci & Res Ctr, Belagavi 590010, India
关键词
Anti-tubercular agents; Antifungal agents; Click chemistry; Molecular docking; 1; 2; 4-Triazole; 3-triazole; Quinoline; 1,2,3-TRIAZOLE DERIVATIVES; 1,3-DIPOLAR CYCLOADDITIONS; BIOLOGICAL EVALUATION; INHIBITORS; DESIGN;
D O I
10.1016/j.bmcl.2021.127984
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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.
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页数:10
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