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

Ali Oubella 1 My Youssef Ait Itto 1 Aziz Auhmani 1 Abdelkhalek Riahi 2 Anthony Robert 2 Jean-Claude Daran 3 Hamid Morjani 4 Carol Parish M'Hamed Esseffar 1
1 Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences
2 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
3 LCC - Laboratoire de chimie de coordination
4 MEDyC - Matrice extracellulaire et dynamique cellulaire - UMR 7369
Abstract : New 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.
Keywords : Isoxazoles Pyrazoles Cycloaddition Diastereoselectivity DFT Cytotoxicity
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Journal articles
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https://hal.univ-reims.fr/hal-02430280
Contributor : Abdelkhalek Riahi <>
Submitted on : Tuesday, January 7, 2020 - 11:18:57 AM
Last modification on : Monday, January 20, 2020 - 8:23:10 AM

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Ali Oubella, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Anthony Robert, et al.. Diastereoselective synthesis and cytotoxic evaluation of new isoxazoles and pyrazoles with monoterpenic skeleton. Journal of Molecular Structure, Elsevier, 2019, 1198, pp.126924. ⟨10.1016/j.molstruc.2019.126924⟩. ⟨hal-02430280⟩

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