Synthesis, structural characterization and density functional studies of ethyl 4-(biphenyl-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate A non-merohedral twinned structure

• Published in: Journal of molecular structure Vol. 1163; pp. 161 - 166
• Main Authors: Yıdırım, Sema Öztürk, Büyükmumcu, Zeki, Butcher, Ray J., Çetin, Gökalp, Şimşek, Rahime, Şafak, Cihat
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05-07-2018
• Subjects: Hexahydroquinoline; Non-merohedral twin; Structural analysis; Non-merohedral twin; Hexahydroquinoline; Structural analysis
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2018.02.103

1,4-Dihydropyridine (1,4-DHP) derivatives have the reducing effect of extracellular Ca2+ ions influx on the L-type calcium channel. Because of this effect many 1,4-DHP derivatives are potent calcium channel blockers and antihypertensive agents. The biphenyl group is present in the structures of the most biologically active compounds and thus is an important group. By introducing this moiety into the structure of various compounds, active compounds are obtained. Thus, pharmacologically active structures can be condensed with the biphenyl structure to achieve novel biologically active compounds or compounds with increased activity. In this study, to achieve an active calcium channel blocker compound, the biphenyl group was introduced into the 1,4-DHP structure. The structure of the compound is proved by IR, 1H NMR, Mass spectroscopy, X-ray crystallography and elemental analysis. The cytotoxic activity assays have continued and positive results have been obtained. The phenyl rings [C16–C21 and C22–C27] make dihedral angles of 84.4 (1) and 87.5 (1)°, respectively, with the 1,4-dihydropyridine ring [N1/C1/C4–C9]. In the crystal, adjacent molecules are linked by NH … O and CH … O hydrogen bonds into chains parallel to [010].
•By introducing biphenyl group into the structure of various compounds, active compounds are obtained.•Thus, pharmacologically active structures can be condensed with the biphenyl structure.•The geometry of the title compound has been optimized by B3LYP.•Frontier orbitals analysis has been performed.•X-ray single-crystal diffraction analysis has been done at low temperature.