Titre :

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

Auteur(s) :

Bimoussa, A. [Auteur]
Oubella, A. [Auteur]
Hachim, M. E. [Auteur]
Fawzi, M. [Auteur]
Itto, M. Y. A. [Auteur]
Mentre, Olivier [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Ketatni, E. [Auteur]
Bahsis, L. [Auteur]
Morjani, H. [Auteur]
Biospectroscopie Translationnelle - EA 7506 [BIOSPECT]
Auhmani, A. [Auteur]

Titre de la revue :

Journal of Molecular Structure

Nom court de la revue :

J. Mol. Struct.

Numéro :

1241

Pagination :

-

Date de publication :

2021-07-21

ISSN :

0022-2860

Mot(s)-clé(s) en anglais :

Sesquiterpene
Crystal structure
Hirshfeld surface analysis
DFT
Cytotoxicity
Spectroscopy

Résumé en anglais : [en]

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 the α,β-unsaturated ...
Lire la suite >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 the α,β-unsaturated sesquiterpene ketone 1 using the azido-Schmidt reaction catalyzed by titanium tetrachloride (TiCl4). The structure of the newly synthesized enaminone 2 was fully identified using its HRMS, FT-IR, UV-Visible, NMR (1H & 13C), and X-ray crystallography analyses. The compounds 1 and 2 were tested for their cytotoxic activity in four human cancer cell lines, fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast (MCF-7 and MDA-MB-231). The obtained results showe that compound 1 is the most active against HT-1080 and A-549 cells with IC50 values from 13.28 to 16.41 µM. The results of theoretical studies used to predict the molecular proprieties that lead to a high potential of cytotoxic effect are in perfect agreement with the experimental results.Lire moins >

Langue :

Anglais

Comité de lecture :

Oui

Audience :

Internationale

Vulgarisation :

Non

Établissement(s) :

Université de Lille
CNRS
Centrale Lille
ENSCL
Univ. Artois

Collections :

• Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Date de dépôt :

2024-01-20T00:35:52Z
2024-02-09T16:10:15Z