Diastereoselective synthesis and cytotoxic evaluation of new isoxazoles and pyrazoles with monoterpenic skeleton

Publication date: 15 December 2019Source: Journal of Molecular Structure, Volume 1198Author(s): Ali Oubella, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Anthony Robert, Jean-Claude Daran, Hamid Morjani, Carol A. Parish, M'hamed EsseffarAbstractNew series of chiral isoxazoles and pyrazoles with monoterpenic skeleton, have been efficiently synthesized from naturally occurring (R)-Carvone, using 1,3-dipolar cycloaddition reaction with arylonitrile oxides and diarylnitrilimines. The reaction showed high peri-, and regioselectivity. In the case of diarylnitrilimines, the reaction revealed to be highly diastereoselective. The structure of the newly synthesized adducts were fully established via spectroscopic analysis and X-ray crystallography. A succinct theoretical study was used to explain the diastereoselectivity experimentally observed. All the newly synthesized monoterpenic isoxazole and pyrazole derivatives were evaluated for their cytotoxic activity against human HT1080, MCF-7 and A-549 cancer cells.Graphical abstractAn efficient and diastereoselective synthesis of new cytotoxic isoxazoles and pyrazoles, using 1,3-dipolar cycloaddition of nitrile oxides and nitrilimines, on naturally occurred (R)-Carvone. Theoretical calculations were carried out using the density functional theory (DFT) to account for the diastereoselectivity of the cycloaddition reactions and all cycloadducts were evaluated for their cytotoxic activity against Human HT1080, MCF-7 and A-549 cancer...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research