Abstract:
Summary: In the current study, 3-formyl phenyl benzenesulfonate is created by reacting 3hydroxybenzaldehyde with benzene sulfonyl chloride, which is aided by triethylamine. Nine unique (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were formed through the reaction of a manufactured 3-formyl phenyl benzenesulfonate chemical with nine 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one, as detailed in the existing literature. Phenyl benzene sulfonate (S) compounds were purchased. Through the reaction of the Schiff bases that were made a secondary amine, such as morpholine with formaldehyde, heterocyclic Mannich bases of a unique kind were created. Five recently found (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4triazol-4-yl)-iminomethyl] compounds are presented in this work. By reacting phenyl benzene sulfonate (S) with morpholine in the presence of formaldehyde, five new (Z)-3-[(3-substituted-1(morpholinomethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were created. Chemical compounds fall under the category of phenylbenzene sulfonates (M). Utilizing IR, 1H NMR, and 13C NMR spectroscopy, fourteen recently novel compounds' chemical structures were examined. The ability of the freshly synthesized Schiff and morpholine-derived Mannich bases to obstruct the aldose reductase enzyme's (AR) activity was also assessed. The 1,2,4-triazole functional group was modified by adding various groups at the 1 and 3 positions, resulting in a collection of compounds (S1-9 and M1, 2, 4, 5, 7). It was determined whether these synthetic compounds could prevent the human recombinant AR enzyme from working in vitro, and the findings were validated using molecular docking, molecular mechanics, and ADME analyses. To better understand this mechanism, synthetic Schiff and Mannich base derivatives as well as the positive control substance quercetin were tested using molecular docking against the human recombinant AR enzyme in vitro. To assess the drug-like properties of Schiff and Mannich base analogs, a series of absorption, distribution, metabolism, and excretion (ADME) properties were analyzed theoretically.
Page(s):
323-335
DOI:
DOI not available
Published:
Journal: Journal of Chemical Society of Pakistan, Volume: 45, Issue: 4, Year: 2023
Keywords:
Schiff base
,
Docking study
,
Benzenesulfonate
,
Mannich Bases
,
4Triazole ring
,
Inhibitory activity