One-pot synthesis, crystal structure, hirshfeld, DFT and anticancer study of ethyl 2-(3-fluoro-4-methylphenyl)-1-propyl-1H-benzo[d]imidazole-5-carboxylate

In the present study, a novel ethyl 2-(3-fluoro-4-methylphenyl)-1-propyl-1H-benzo[d]imidazole-5-carboxylate was synthesized by an efficient one-pot nitro reductive cyclization method using sodium dithionite as reductive cyclizing agent in DMSO medium. Title compound was recrystallized in Dimethyl formamide solvent. Single crystal X-ray studies revealed that the title compound crystallized in monoclinic system (P21/c space group with Z = 4) and molecules are linked with C—H…O intermolecular hydrogen bonds. The Hirshfeld surfaces computational method applied to visualize and analyze the intermolecular interactions within the crystal structure. The theoretical structural optimization of the title compound was carried out using B3LYP/6-311++G (d,p) level of theory. Anticancer screening result of compound showed promising activity against human malenoma A375 and mouse malenoma B16F10 cancer cell line with IC50 value of 33.99 μM and 31.14 μM in comparison to the standard drug Cisplatin with IC50 12.99 μM and 20.33 μM respectively. [Display omitted]