Synthesis, DFT and molecular docking of novel benzamide as elastase inhibitor

A new compound, C.sub.23H.sub.20BrN.sub.3OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P - 1 space group, with dimensions of a = 9.2304 (6) â«, b = 11.1780 (8) â«, c = 11.3006 (6) â«, [alpha] = 107.146 (5)[degrees], [beta] = 93.701 (5)[degrees], [gamma] = 110.435 (6)[degrees], Z = 2 and V = 1025.61 (12) â«.sup.3. The crystal structure showed that C-H***N and C-H***O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R.sub.2.sup.2(14) and R.sub.2.sup.2(16) ring motifs. The Hirshfeld surface analysis revealed that H...H (44.1%) and H...C/C...H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 [micro]M. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.