Design, Synthesis and Molecular Docking Studies of Novel Triazole‐Chromene Conjugates as Antitubercular, Antioxidant and Antifungal Agents

Abstract

A green and efficient protocol has been developed for the synthesis of novel 1,2,3‐triazole‐chromene conjugates (7 a‐j) via ultrasound assisted and NaHCO3 catalyzed for the first time. Structures of all the new conjugates were deduced by various spectroscopic techniques. The newly synthesized triazole‐chromene conjugates were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain. The conjugates 7 f and 7 h were found to be most active with MIC value 12.5 μg/mL. Furthermore, all the conjugates were screened for their antioxidant activity and are highly active (IC50=7.05‐14 μg/mL) than the reference drug BHT (16.47 μg/mL). The triazole‐chromene conjugates were also screened for their in vitro antifungal activity and some of the conjugates 7 a, 7 b, 7 d, 7 e, 7 f and 7 i were exhibited potent activity (MIC=6.25‐25 μg/mL) than the reference drug Miconazole. Docking studies showed significant binding affinity in the active site of Mycobacterium tuberculosis DprE1 enzyme.

Synthesis, antibacterial, and antioxidant activities of naphthyl‐linked disubstituted 1,2,3‐triazoles

“…The synthesized compounds were screened for free radical scavenging activity by 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) assay . 1 mL of various concentrations of the test compounds (20, 40, 60, 80, and 100 μg/mL) in methanol was added to 1 mL of methanolic solution of DPPH (0.004 g DPPH in 100 mL methanol).…”

“…Synthesized disubstituted triazoles were evaluated for in vitro free radical scavenging activity. The antioxidant activity of compounds ( 7a ‐ 7o ) resulted by using the DPPH radical scavenging assay and the results are summarized in Table .…”

Benzopyran-Core as an Antimycobacterial Agent

“…The results demonstrate that triazole-chromene hybrids with a fluoro substituted aniline are more active than the other compounds and 6-chloro substitution on the chromene ring improves activity while 6-bromo substitution was unfavorable for antitubercular activity. Khare et al [72] synthesized 1,2,3-triazolechromene conjugates and evaluated them for their in vitro antitubercular activity against Mtb H 37 Rv strain. Compounds 31 (a-b) were the most effective in terms of inhibiting mycobacterial growth with MIC=12.5µg/mL.…”

An elegant and efficient synthesis of heterocycles integrated with bis‐N‐acyl pyrazoline and bis‐1, 2, 3‐triazole via a green synthetic methodology

“…On the other hand, good aqueous solubility of 1,2,3-triazoles in biological system may further elevate the potentiality, namely, anti-HIV [18], antifungal [19], antimicrobial [20], and anticancer [21] activities. Recently, the development of hybrid molecules having more than one pharmacophore has gained much interest in the field of drug development, thus resulting in hitherto unknown bioactive heterocyclic hybrids with potent activities [22,23].…”