Abstract
In the title racemic compound, ethyl 4-(4-di-methyl-amino-phen-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate, the common structural features in this type of compound, such as the flat-boat conformation of the 1,4-di-hydro-pyridine (1,4-DHP) ring, the envelope conformation of the fused cyclo-hexa-none, and the substituted phenyl ring at the pseudo-axial position and orthogonal to the 1,4-DHP ring, are present. In the crystal, mol-ecules are linked via N-H⋯O and C-H⋯O hydrogen bonds, forming layers parallel to the (10) plane.
Highlights
In the title racemic compound, ethyl 4-(4-dimethylaminophenyl)-2,7,7trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, the common structural features in this type of compound, such as the flat-boat conformation of the 1,4-dihydropyridine (1,4-DHP) ring, the envelope conformation of the fused cyclohexanone, and the substituted phenyl ring at the pseudo-axial position and orthogonal to the 1,4-DHP ring, are present
1,4-Dihydropyridine (DHP) derivatives are well known for their calcium-channel blocking activity and many of these compounds, such as nifedipine, nicardipine, and amlodipine, have been used in the treatment of angina pectoris and systemic hypertension. (Wishart et al, 2006) 4-Aryl-1,4-dihydropyridines that bind the L-type voltage-gated calcium channels (VGCC) have been in general medical practice for over three decades (Zamponi, 2005)
DHP derivatives, i.e. 4-aryl-hexahydroquinolones, we report the crystal structure of a compound we synthesized, ethyl
Summary
1,4-Dihydropyridine (DHP) derivatives are well known for their calcium-channel blocking activity and many of these compounds, such as nifedipine, nicardipine, and amlodipine, have been used in the treatment of angina pectoris and systemic hypertension. (Wishart et al, 2006) 4-Aryl-1,4-dihydropyridines that bind the L-type voltage-gated calcium channels (VGCC) have been in general medical practice for over three decades (Zamponi, 2005). Many modifications on 1,4-DHP have been performed to obtain active compounds as calcium-channel agonists or antagonists (Martın et al, 1995; Rose, 1990; Rose & Drager 1992) One such modifications is fusing a cyclohexanone ring to form hexahydroquinolone, in which the orientation of the carbonyl group of the ester substituent at the 5-position in the 1,4-DHP ring has been fixed. This class of compounds has been shown to have moderate calcium-channel antagonistic activity, as well as antiinflammatory modes and stem-cell differentiation properties, and has been implicated in slowing neurodegenerative disorders (Trippier et al, 2013).
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