Click Chemistry Inspired Design, Synthesis and Molecular Docking Studies of Coumarin, Quinolinone Linked 1,2,3‐Triazoles as Promising Anti‐Microbial Agents

Abstract

A series of new coumarin, quinolinone and benzyl linked 1,2,3‐triazole derivatives have been synthesized and screened for their anti‐bacterial and anti‐fungal activities. Results of bioassay indicate that, compounds containing chloro and methoxy substituents in coumarin (6 j), chloro substitution in quinolinone (7 g) and 3‐chloro benzyl analogue (8 f) exhibit excellent anti‐bacterial activities. The results of anti‐fungal activities also reveal that methoxy and chloro substituted coumarins (6 e and 6 j) were highly active against yeast strains. In addition, chloro and methyl substituted coumarins (6 h and 6 i) were also exhibited excellent activity. Further, methyl substituted quinolinone with chloro substituted coumarin (7 f) was found to highly active against yeast fungi and filamentous strain A.niger. It is evident from the results obtained and SAR studies that electron withdrawing or donating character of the substituents do not seem to be a major factor in increasing or decreasing anti‐microbial activity.

Application of triazoles in the structural modification of natural products

“…A series of new coumarin-, quinolinone-, and benzyl-linked 1,2,3-triazole derivatives were synthesised and screened for their antibacterial and antifungal activities by Savanur and et al. 133 Most of the compounds exhibited good activity in against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis and the Gram-negative bacteria Pseudomonas aeruginosa . Almost all of the compounds exhibited very good antifungal activity.…”

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

“…2). 16 In 2018, various biological screenings were conducted [17][18][19][20] which led to the identification of anticancer, [21][22][23] antimicrobial, [24][25][26][27][28] anti-infective, 29,30 and antioxidant [31][32][33] properties of the studied 1,2,3-triazole-bearing hybrids. Moreover, triazole-linked derivatives were suggested to affect adenosine diphosphate ribosylation biology, 34 and were used widely in peptides to mimic a trans-amide bond, despite their hazardous effects on native peptide activity.…”

New 1,2,3-Triazole-Containing Hybrids as Antitumor Candidates: Design, Click Reaction Synthesis, DFT Calculations, and Molecular Docking Study

“…The basic unit existing in a numerous medicinal drug is mainly 1,2,3-triazole and/or 1,2,4-triazole moieties ( Figure 1 ), and their analogies have attracted endless interest in the field of medicinal chemistry. Triazole-containing heterocycles are architectures used for the construction of lead molecules, attracting the interest of researchers owing to their wide range of biological impacts, especially as anticancer [ 3 ], antimicrobial [ 4 ], anti-tubercular [ 5 ], anticonvulsant [ 6 ], antibacterial [ 7 ], anti-inflammatory [ 8 ], analgesic [ 9 ], antiviral [ 10 ], and anti-HIV agents [ 11 ].…”