The title compounds, C20H21F2NO3 and C21H23F2NO3, respectively, belong to a class of 1,4-dihydropyridines whose members sometimes display calcium modulatory properties. The 1,4-dihydropyridine rings have the usual shallow boat conformation. In each structure, the 2,3-difluorophenyl ring is oriented such that the fluoro substituents are in a synperiplanar orientation with respect to the 1,4-dihydropyridine ring plane and the oxocyclohexene ring has a slightly distorted envelope conformation. Both structures exhibit the same intermolecular N-H...O hydrogen-bonding motif, in which the molecules are linked into chains by interactions involving the carbonyl O atom of the oxocyclohexene ring.
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Two 1,4-dihydropyridine derivatives with potential calcium-channel antagonist activity.
Acta Crystallogr C
February 2011
Institute of Organic Chemistry, University of Zürich, Switzerland.
The title compounds, benzyl 4-(3-chloro-2-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate, C(23)H(19)ClFNO(3), (I), and 3-pyridylmethyl 4-[2-fluoro-3-(trifluoromethyl)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C(26)H(24)F(4)N(2)O(3), (II), belong to a class of 1,4-dihydropyridines whose members sometimes display calcium modulatory properties. The 1,4-dihydropyridine ring in each structure has a shallower than usual shallow-boat conformation and is nearly planar in (I). In each structure, the halogen-substituted benzene ring is oriented such that the halogen substituents are in a synperiplanar orientation with respect to the 1,4-dihydropyridine ring plane.
View Article and Find Full Text PDF(+/-)-Methyl and (+/-)-ethyl 4-(2,3-difluorophenyl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate.
Acta Crystallogr C
December 2005
Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland.
The title compounds, C20H21F2NO3 and C21H23F2NO3, respectively, belong to a class of 1,4-dihydropyridines whose members sometimes display calcium modulatory properties. The 1,4-dihydropyridine rings have the usual shallow boat conformation. In each structure, the 2,3-difluorophenyl ring is oriented such that the fluoro substituents are in a synperiplanar orientation with respect to the 1,4-dihydropyridine ring plane and the oxocyclohexene ring has a slightly distorted envelope conformation.
View Article and Find Full Text PDFN,N-Diethyl-2,6,6-trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide.
Acta Crystallogr C
July 2002
Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland.
The title compound, C(23)H(29)N(3)O(4), has potential calcium modulatory properties. The conformation of the 1,4-dihydropyridine ring is unusual in that it is planar, instead of the usual shallow boat. The 3-nitrophenyl substituent is in the synperiplanar orientation with respect to the dihydropyridine ring plane.
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