RESUMEN
The title compound N-(4-meth-oxy-phen-yl)-2-[4-(3-oxo-3-phenyl-prop-1-en-1-yl)phen-oxy]acetamide, C24H21NO4, was prepared from reaction of N-(4-meth-oxy-phen-yl)-2-chloro-acetamide and (E)-3-(4-hy-droxy-phen-yl)-1-phenyl-prop-2-en-1-one, which was obtained from the reaction of 4-hy-droxy-benzaldehyde and aceto-phenone. The structure of the title compound was determined by IR, 1H-NMR, 13C-NMR and HR-MS spectroscopic data and further characterized by single-crystal X-ray diffraction. The asymmetric unit contains four mol-ecules, each displaying an E-configuration of the C=C bond. The dihedral angle between the phenyl rings in each mol-ecule varies between 14.9â (2) and 45.8â (2)°. In the crystal, C-Hâ¯O hydrogen-bonding inter-actions link the mol-ecules into chains running along the [001] direction. In addition, C-Hâ¯π inter-actions further stabilize the crystal packing. A Hirshfeld analysis indicates that the most important contributions to the surface contacts are from Hâ¯H (43.6%), Câ¯H/Hâ¯C (32.1%) and Oâ¯H/Hâ¯O (18.1%) inter-actions.
RESUMEN
The syntheses of nine new 5-iodosalicylic acid-based 1,3,4-oxadiazoline derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6a), 2-[4-acetyl-5-methyl-5-(4-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6b), 2-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate, C19H17IN2O4 (6c), 2-[4-acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16FIN2O4 (6d), 2-[4-acetyl-5-(4-chlorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16ClIN2O4 (6e), 2-[4-acetyl-5-(3-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6f), 2-[4-acetyl-5-(4-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6g), 2-[4-acetyl-5-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6h) and 2-[5-(4-acetamidophenyl)-4-acetyl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6i). The compounds were characterized by mass, 1H NMR and 13C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c, 6d and 6e. Compounds 6c and 6d are isomorphous, with the 1,3,4-oxadiazoline ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C-H...O, C-H...π and I...π interactions. For 6e, the 1,3,4-oxadiazoline ring is almost planar. In the packing, Cl...π interactions are observed, while the I atom is not involved in short interactions. Compounds 6d, 6e, 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC50 values of 0.9-4.5â µM.