Synthesis of New 1H-1,2,3-Triazole Analogs in Aqueous Medium via Click Chemistry: A Novel Class of Potential Carbonic Anhydrase-II Inhibitors

A series of novel 1H-1,2,3-triazole analogs (9a-j) were synthesized via Click chemistry and Suzuki-Miyaura cross-coupling reaction in aqueous medium. The compounds were evaluated for their carbonic anhydrase-II enzyme inhibitory activity in vitro. The synthesis of triazole 7a was accomplished using (S)-(-) ethyl lactate as a starting material. This compound (7a) underwent Suzuki-Miyaura cross-coupling reaction with different arylboronic acids in aqueous medium to afford the target molecules, 9a-j in good yields. All newly synthesized compounds were characterized by H-1 NMR, C-13 NMR, FT-IR, HRMS, and where applicable F-19 NMR spectroscopy (9b, 9e, 9h, and 9j). The new compounds have shown moderate inhibition potential against carbonic anhydrase-II enzyme. A preliminary structure-activity relationship suggested that the presence of polar group at the 1H-1,2,3-triazole substituted phenyl ring in these derivatives (9a-j) has contributed to the overall activity of these compounds. Furthermore, via molecular docking, it was deduced that the compounds exhibit inhibitory potential through direct binding with the active site residues of carbonic anhydrase-II enzyme. This study has unraveled a new series of triazole derivatives as good inhibitors against carbonic anhydrase-II.

Automated summary

A series of novel 1H-1,2,3-triazole analogs were synthesized via Click chemistry and Suzuki-Miyaura cross-coupling reaction, showing moderate inhibition potential against carbonic anhydrase-II enzyme. The presence of polar group at the 1H-1,2,3-triazole substituted phenyl ring in these derivatives was found to contribute to the overall activity of these compounds. Through molecular docking, it was deduced that the compounds exhibit inhibitory potential through direct binding with the active site residues of carbonic anhydrase-II enzyme.