Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

A new compound, C23H20BrN3OS, 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) A, b = 11.1780 (8) A, c = 11.3006 (6) A, & alpha; = 107.146 (5)& DEG;, & beta; = 93.701 (5)& DEG;, & gamma; = 110.435 (6)& DEG;, Z = 2 and V = 1025.61 (12) A(3). The crystal structure showed that C-H & BULL;& BULL;& BULL;N and C-H & BULL;& BULL;& BULL;O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R-2(2)(14) and R-2(2)(16) ring motifs. The Hirshfeld surface analysis revealed that H horizontal ellipsis H (44.1%) and H horizontal ellipsis C/C horizontal ellipsis 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 & mu;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.

Automated summary

A new compound, C23H20BrN3OS, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound showed potential as a novel inhibitor of elastase enzyme, exhibiting stronger activity than oleanolic acid. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.