RESUMO
In the title compound, C31H28O4, the phenyl rings of the chalcone unit subtend a dihedral angle of 26.43â (10)°. The phenyl rings of the pendant benz-yloxy groups are orientated at 75.57â (13) and 75.70â (10)° with respect to their attached ring. In the crystal, weak C-Hâ¯O and C-Hâ¯π inter-actions link the mol-ecules. The inter-molecular inter-actions were qu-anti-fied and analysed using Hirshfeld surface analysis, which showed a breakdown into Hâ¯H (49.8%), Hâ¯C/Câ¯H (33.8%) and Hâ¯O/Oâ¯H (13.6%) inter-actions with other types making negligible contributions.
RESUMO
Isophorone is a cyclic ketone that has gained significant attention in the field of organic chemistry due to its versatile reactivity and structural attributes. Derivatives of isophorone offer a broad spectrum of applications ranging from pharmaceuticals to polymer chemistry. With the aim of developing novel hybrid structures based on benzylidene by combining with isophorone scaffold, we report 3 derivatives of the benzylidene-isophorone hybrids and its potent anticancer activity. In order to optimize the anticancer activity of hybrids di-substitution of -Cl group in C2 and C6 position of phenyl ring (compound1), -OCH3 group in C2 and C5 position of phenyl ring (compound2), and -OCH3 group in C2 and C3 position of phenyl ring (compound3) of benzylidene (PhCH=) moiety were made. The structure of Compounds1,2 and 3 were elucidated using spectral and XRD methods. Compounds1,2 and 3 exhibit space group P c a 21, P-1, and P 1 21/n 1 respectively. Compounds1,2 and 3 were tested for the potent anticancer activity on MDA MB-231 cell line. All the three compounds exhibit good anticancer activity on the breast cancer cells. The parent hybrid with ortho, ortho directing -Cl (1) exhibits strong antiproliferation effect (IC50 = 0.028 µM) on MDA-MB 231 cell line. However, hybrid structures with ortho, meta directing -OCH3 (2) group showed moderate effect (IC50 = 0.061 µM) and hybrid with ortho, meta directing -OCH3 (3) substitution showed the least potent anticancer activity (IC50 = 0.074 µM). The benzylidene-isophorone hybrids exhibit anticancer effects in the following order: 1 > 2 > 3.
Assuntos
Antineoplásicos , Compostos de Benzilideno , Humanos , Antineoplásicos/farmacologia , Antineoplásicos/química , Linhagem Celular Tumoral , Compostos de Benzilideno/farmacologia , Compostos de Benzilideno/química , Proliferação de Células/efeitos dos fármacos , Modelos Moleculares , Cristalografia por Raios X , CicloexanonasRESUMO
In the title compound, C22H23N3O2, the cyclo-hexane ring adopts a chair conformation. The methyl-phenyl ring is oriented at an angle of 36.2â (1)° with respect to the best plane of cyclo-hexane moiety. In the crystal, mol-ecules associate via C-Hâ¯N hydrogen bonds, forming a three-dimensional network.
RESUMO
In the title pyrrolizidine derivative, C33H26F2N2O2, both pyrrolidine rings of the pyrrolizidine moiety adopt an envelope conformation. The di-fluoro-phenyl group is oriented at an angle of 54.3â (1)° with respect to the oxindole moiety. The crystal packing features an N-Hâ¯O hydrogen bond, which forms an R 2 (2)(8) motif, and a C-Hâ¯O inter-action, which generates a C(8) chain along [010]. In addition, this chain structure is stabilized by C-Hâ¯π inter-actions. In one of the pyrrolidine rings, the methyl-ene group forming the flap of an envelope and the H atoms of the adjacent methyl-ene groups are disordered over two sets of sites, with site-occupancy factors of 0.571â (4) and 0.429â (4).