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The effect of bromine scanning around the phenyl group of 4‐phenylquinolone derivatives
Author(s) -
Steiger Scott A.,
Monacelli Anthony J.,
Li Chun,
Hunting Janet L.,
Natale Nicholas R.
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614015617
Subject(s) - bromine , group (periodic table) , chemistry , mathematics , medicinal chemistry , organic chemistry
Three quinolone compounds were synthesized and crystallized in an effort to study the structure–activity relationship of these calcium‐channel antagonists. In all three quinolones, viz. ethyl 4‐(4‐bromophenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate, (I), ethyl 4‐(3‐bromophenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate, (II), and ethyl 4‐(2‐bromophenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate, (III), all C 21 H 24 BrNO 3 , common structural features such as a flat boat conformation of the 1,4‐dihydropyridine (1,4‐DHP) ring, an envelope conformation of the fused cyclohexanone ring and a bromophenyl ring at the pseudo‐axial position and orthogonal to the 1,4‐DHP ring are retained. However, due to the different packing interactions in each compound, halogen bonds are observed in (I) and (III). Compound (III) crystallizes with two molecules in the asymmetric unit. All of the prepared derivatives satisfy the basic structural requirements to possess moderate activity as calcium‐channel antagonists.