Synthesis, biological evaluation and molecular docking studies of N-acylheteroaryl hydrazone derivatives as antioxidant and anti-inflammatory agents

Abstract

In search of new therapeutics with greater potency, three new series of 3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carbohydrazide derivatives have been synthesized and evaluated for their in vitro antioxidant and anti-inflammatory activities. The hydrazones bearing a core pyrazole, chromone and tetrazolo[1,5-a]quinoline scaffold showed promising activities. Interestingly, compounds 3a (EC 50 = 06.00 ± 2.36) and 5c (EC 50 = 07.21 ± 0.67) showed the most potent antioxidant activity, while compounds 3a (EC 50 = 10.25 ± 1.08), 7b (EC 50 = 10.50 ± 0.99) and 7c (EC 50 = 11.18 ± 0.15) showed significant anti-inflammatory activity. Furthermore, molecular docking studies also revealed a significant correlation between the binding score and biological activity for these compounds to describe the molecular basis for the structure activity relationship (SAR) results. As these compounds are good cyclooxygenase inhibitors, isoenzyme inhibitory potency studies are warranted.

Synthesis of Chromone-Related Pyrazole Compounds

“…Gill and coworkers reported the reaction of substituted 3-formylchromones with 3-methyl-1-phenyl-1 H -thieno[2,3- c ]pyrazole-5-carbohydrazide using acetic acid as catalyst in methanol which gave the corresponding hydrazides in good yield (78–81%) [ 49 ]. Two of the four synthesized compounds showed promising antioxidant and anti-inflammatory activities [ 49 ].…”

Advances in the site-selective C-5, C-3 and C-2 functionalization of chromones via sp2 C–H activation

“…1 The importance of chromones in drug discovery and synthetic transformations is evident from a number of publications in the eld. Chromones are well documented in the literature owing to their interesting biological applications such as anticancer, 2-5 antimicrobial, [6][7][8][9][10] anti-inammatory, [11][12][13][14] antioxidant, [15][16][17][18] anti-Alzheimer, [19][20][21][22] and antidiabetic [23][24][25][26] activities. Apart from their biological applications, they show promising uorescent activity, and hence can be used as sensors in detecting various metal ions and in bioimaging.…”

An Organocatalyzed Efficient One‐pot Synthesis, Biological Evaluation, and Molecular Docking Studies of 4,4′‐(Arylmethylene)bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols)

“…Recently, we have reported our work on pyrazole containing compounds with their molecular docking [22]. In continuation of this work, and our continuous focus on safe and potent synthesis of biologically active heterocycles [23][24][25][26], herein we report a simple and facile multicomponent one-pot synthesis of 4,4′-(arylmethylene)bis (3-methyl-1-phenyl-1H-pyrazol-5-ols) (Scheme 1), using ʟ-proline as an organocatalyst with their potential antimicrobial, antioxidant, and anti-inflammatory activities.…”