Synthesis of new coumarin derivatives containing aminobenzotriazole, triazole moieties and their antimicrobial activities

Abstract

Background: Coumarins are structural units of several natural products and feature widely in pharmacologically and biologically active compounds. Their derivatives are characterized by excellent chemical reactivity and different bioactivity. Objective: The present work aims to design and synthesise new coumarin derivatives bearing 2-aminobenzotriazole, 2-amino-5-mercapto-1,3,4-thiadiazole moieties. Moreover, this study also includes testing of target compounds in order to assay their antibacterial and antifungal activities. Methods: This includes the synthesis of coumarin-3-carboxylic acid (compound 2), 2-aminobenzotriazole (compound 3), 2-amino-5-mercapto-1,3,4-thiadiazole (compound 5) and followed by a challenge of coupling between steric heterocycles compounds (2 with 3) and (2 with 5). In this study, the chemical structures of these new coumarin derivatives were investigated and identified by their physicochemical properties, spectroscopic FTIR and CHNS &O elemental microanalysis techniques in France. Results: Coumarin-3-carboxylic acid, 2-aminobenzotriazole and 2-amino-5-mercapto-1,3,4-thiadiazole are the key intermediates required to prepare the target products. Conclusion: The development of bacterial resistance has led to the synthesis of newer, more potent, and complex coumarin derivatives. It was observed that when an amine group containing a heterocyclic compound was introduced to the carboxylic side, comparable antimicrobial activity against organisms was achieved from the levofloxacin nucleus.