Search

A series of mono and bis -triazole coumarin hybrids 6a–u and 9a–f respectively have been synthesized using 4-(azidomethyl)-2 H -chromen-2-ones 5a–i and aryl propargyl ethers 2a–c/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6a–u with MIC 50–100 μg/mL, whereas the bis compounds 9a–f were more effective with MICs between 0.2 and 12.5 μg/mL. Molecular modeling and 3D-QSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The bis compound 9b showed excellent activity with MIC value as low as 0.2 μg/mL. [ABSTRACT FROM AUTHOR]

[Display omitted] • Novel quinoline and 1,2,4-triazole appended triazole derivatives were conceived. • Microwave synthesis resulted transitory reaction times, exceptional yields and purity. • The reported compounds proclaimed excellent anti-tubercular activity. • All the compounds exhibited exceptional antifungal activity. Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4 H)-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 CuSO 4 ·5H 2 O 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. [ABSTRACT FROM AUTHOR]