Synthesis, characterization and pharmacological study of some Novel Nsubstituted derivatives of 7-(3-(3-(trifluoromethyl)phenyl)allylidene)-3-(3- (trifluoromethyl)styryl)-3,3a,4,5,6,7-hexahydro-2H-indazole
In the present study, a novel series of N-substituted 3,3a,4,5,6,7-hexahydro-2H-indazole derivatives bearing trifluoromethyl-substituted styryl and phenyl allylidene moieties were successfully designed, synthesized, and evaluated for their pharmacological potential. The synthetic strategy involved a three-step protocol comprising base-catalysed Claisen–Schmidt condensation, hydrazone-mediated cyclization, and selective N-acylation, affording the target derivatives in moderate to excellent yields. Structural elucidation of all synthesized compounds was accomplished using UV–Visible, FT-IR, ¹H and ¹³C NMR spectroscopy, and LC–MS analysis, confirming the successful formation of the hexahydroindazole scaffold and subsequent N-functionalization. The pharmacological evaluation focused on in vitro cytotoxic activity against MCF-7 (breast), HepG2 (liver), and A549 (lung) cancer cell lines using the MTT assay, along with wound scratch assays on L929 fibroblast cells to assess regenerative potential. Among the tested compounds, derivatives 3a and 3b exhibited significant, concentration-dependent cytotoxic effects across all cancer cell lines, with compound 3b demonstrating superior anticancer potency, as reflected by lower IC₅₀ values. The enhanced activity of compound 3b is attributed to the acetyl substitution at the N-position, which optimizes lipophilicity and steric accessibility. In contrast, compound 3a displayed pronounced wound-healing activity, promoting fibroblast migration and accelerated scratch closure without inducing cytotoxicity in normal cells. Overall, the study highlights the critical influence of N-substitution and trifluoromethyl incorporation on biological activity and identifies N-substituted hexahydro-2H-indazole derivatives as promising lead candidates for further development as anticancer and regenerative therapeutic agents.