Abstract
A variety of benzimidazole by the heterocyclization of orthophenylenediamine were synthesized in 69–86% yields. The synthesized compounds 3a-f and 6a-f were characterized and further investigated as jack bean urease inhibitors. Density functional theory (DFT) studies were performed utilizing the basis set B3LYP/6-31G (d, p) to acquire perception into their structural properties. Frontier molecular orbital (FMO) analysis of all compounds 3a–f and 6a-f was computed at the same level of theory to get a notion about their chemical reactivity and stability. The mapping of the molecular electrostatic potential (MEP) over the entire stabilized molecular geometry indicated the reactive centers. They exhibited urease inhibition activity with IC50 between 22 and 99 μM. Compounds containing withdrawing groups on the benzene ring (3d, 6d) were not showing significant urease inhibition. The value obtained for 3a, 3b, 3f had shown their significant urease inhibition for both theoretical and experimental. Notably, the compound having S-configuration (3a) (22.26 ± 6.2 μM) was good as compared to its R enantiomer 3f (31.42 ± 23.3 μM). Despite this, we elaborated the computational studies of the corresponding compounds, to highlight electronic effect which include HOMO, LUMO, Molecular electrostatic potential (MEP) and molecular docking.
Highlights
Benzimidazoles are well known nitrogen-containing bioactive compounds
The iso-density in highest occupied molecular orbital (HOMO) of 3a, 3f is mainly spread only to the rings, which reflects less conjugation. This observation indicates that the HOMO-lowest unoccupied molecular orbital (LUMO) gap in 3a, 3f should display the highest energy among all products studied, and this was the case
Chiral derivatives of benzimidazoles have been synthesized to validate their role in jack bean urease inhibition
Summary
Benzimidazoles are well known nitrogen-containing bioactive compounds. They showed a variety of activities including anti-diabetic [1], antimicrobial [2], antifungal [3], antiviral [4], anti-cancer activity [5a,b] and anthelminthic [6]. Benzimidazoles as jackbean urease inhibitors and their DFT studies have rarely ever found in the literature In this context, some chiral derivatives of benzimidazoles of benzimidazoles were synthesized, several quantum chemical descriptors in order to interpret various molecular properties such as electronic structure, stability, reactivity, in the interest of determining how they could have an impact on our understanding of the experimental observations and describing various aspects of chemical binding. Some chiral derivatives of benzimidazoles of benzimidazoles were synthesized, several quantum chemical descriptors in order to interpret various molecular properties such as electronic structure, stability, reactivity, in the interest of determining how they could have an impact on our understanding of the experimental observations and describing various aspects of chemical binding The comparative inhibitory activity of the most potent enantiomer was calculated
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