New enaminone sesquiterpenic: TiCl4-catalyzed synthesis, spectral characterization, crystal structure, Hirshfeld surface analysis, DFT studies and cytotoxic activity

In this work, the compound 2 named ethyl (1,1-dichloro-1a,5,5,7-tetramethyl-8-oxo-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-6-yl)glycinate (C20H29Cl2NO3) was synthesized from ?,?-unsaturated sesquiterpene ketone 1 using azido-Schmidt reaction catalyzed by titanium tetrachloride (TiCl4). The structure of newly enaminone fully identified its HRMS, FT-IR, UV-Visible, NMR (1H & 13C), and X-ray crystallography analyses. compounds were tested for their cytotoxic activity in four human cancer cell lines, fibrosarcoma (HT-1080), lung carcinoma (A-549), breast (MCF-7 MDA-MB-231). obtained results showe that is most active against HT-1080 A-549 cells with IC50 values 13.28 to 16.41 µM. theoretical studies used predict molecular proprieties lead a high potential effect are perfect agreement experimental results.