Abstract

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 1H NMR, 13C NMR, FT-IR, HRMS, and where applicable 19F 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.

Highlights

  • 1H-1,2,3-Triazole molecules play a vital role in pharmaceuticals and agrochemicals (Abdel-Wahab et al, 2012)

  • A series of novel 1H-1,2,3-triazole analogs were synthesized (9a–j) and evaluated for their carbonic anhydrase-II inhibitory activity in vitro. (S)-(-) Ethyl lactate was used as a starting material to introduce the chirality of the target molecules

  • All the compounds have shown moderate inhibition potential against carbonic anhydrase-II enzyme reported for the first time

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Summary

Introduction

1H-1,2,3-Triazole molecules play a vital role in pharmaceuticals and agrochemicals (Abdel-Wahab et al, 2012). The chemistry of the compounds containing this moiety underwent substantial growth over the past decades (Thirumurugan et al, 2013). These compounds are widely used in industrial applications such as dyes, photographic materials, photostabilizers, agrochemicals, and corrosion inhibitors (copper alloys) (Fan et al, 1996). There are fifteen isoforms of CA which have been identified so far (Lindskog, 1997; Aggarwal et al, 2013) They possess a difference in their organ distributions, levels of gene expression, molecular sequence features, and kinetic parameters (Krishnamurthy et al, 2008). CAs are key contributors to various physiological and pathological processes. They are considered the prime therapeutic target for the treatment of several chronic diseases

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