Crystal structure of a calcium channel antagonist: 4-(2,4-dichlorophenyl)-N,N,N',N'-tetraethyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamide

Mehdi, Safia; Ravikumar, K.

doi:10.1107/s0108270192001446

Cited by 6 publications

(3 citation statements)

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“…1,4-Dihydropyridine derivatives (1,4-DHPs) form a class of heterocyclic compounds with interesting pharmacological and biological properties [1][2][3][4][5][6][7][8][9]. It is well known that the 1,4-DHP nucleus serves as the scaffold of important cardiovascular drugs and it has been well established that the calcium modulator activity of this family of compounds is determined by structural requirements [10][11][12][13][14]. The systematic structural modification of the 1,4-DHP ring yields different compounds used in the treatment of hypertension and angina pectoris [15][16][17][18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine

et al. 2011

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The synthesis of a novel unsymmetrical dihydropyridine, bearing carboxy methyl and carbomethoxy groups at C(3) and C(5), respectively, has been achieved by applying the modified Hantzsch-type condensation, which involves the Michael addition of Knoevenagel adduct with an enamine. The product obtained was characterized by spectroscopic techniques and finally confirmed by X-ray diffraction studies. The title compound C 17 H 19 NO 3 crystallizes in Monoclinic crystal class in space group P2 1 /c with cell parameters a = 9.9130(12) Å , b = 7.3320(5) Å , c = 22.018(3) Å , b = 109.637(3)°, V = 1507.2(3) Å 3 and Z = 4. The final residual factor R 1 = 0.0642. The structure exhibits both intra and inter-molecular hydrogen bonding of the type C-HÁÁÁO and N-HÁÁÁO. The pyridine ring gives boat conformation.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine

et al. 2011

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“…All of the nifedipine derivatives examined by singlecrystal X-ray diffraction (Triggle, Langs & Janis, 1989;Mehdi & Ravikumar, 1992) exhibit a flattened-boat conformation of the 1,4-dihydropyridine ring with the N atom at the prow and the phenyl ring in pseudoaxial position at the bow. Structure-activity studies have demonstrated that flattening of the boat conformation correlates with increased activity, presumably due to the concurrent change in position of the phenyl ring.…”

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confidence: 99%

Dibutyl 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, Diisobutyl 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and Di-tert-butyl 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Rowan¹,

Holt²

1996

Acta Crystallogr C

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The structures of dibutyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, C23H30N206, diisobutyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, C23H30N206, and di-tertbutyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, C23H30N206, members of the 1,4-dihydropyridine class of calcium antagonists, have been determined. Increasing the bulk of the esterification groups, as quantified in a cone-angle analysis, leads to greater perpendicularity of the dual ring system. This leads to conclusions about the potential activity of these compounds. Comment AbstractThe structures of (E)-6-chloro-3-[2-(4-chlorophenylsulfonyl)ethenyl]-4-chromanone, CITHIoC1204S, (E)-6bromo-3-[2-(4-bromophenylsulfonyl)ethenyl]-4-chromanone, C17HIoBr2OnS, and (E)-3-[2-(4-chlorophenylsulfonyl)ethenyl ]-6-methoxy-4-chromanone, C 18 H 13 C105 S, display similar bond angles and distances, but differ in the conformations of the ring systems.

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“…In all of the 1,4-dihydropyridine-ring-containing nifedipine derivatives examined by single-crystal X-ray diffraction (Triggle, Langs & Janis, 1989;Mehdi & Ravikumar, 1992), the 1,4-dihydropyridine ring exhibits a boat conformation with the N atom at the prow and the phenyl ring in an axial position at the bow. Structure-activity studies have demonstrated that flattening of the boat conformation correlates with increased activity, presumably due to the concurrent change in position of the phenyl ring.…”

mentioning

confidence: 99%

3,5-Dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrosophenyl)pyridine and Dichlorobis[3,5-dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)pyridine]copper(II)

Rowan¹,

Holt²

1995

Acta Crystallogr C

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Crystal structure of a calcium channel antagonist: 4-(2,4-dichlorophenyl)-N,N,N',N'-tetraethyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamide

Cited by 6 publications

References 0 publications

Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine

Synthesis, Characterization, Crystal and Molecular Structure Analysis of 2,6-Dimethyl-3-Acetyl-5-Carbomethoxy-4-Phenyl-1,4-Dihydropyridine

Dibutyl 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, Diisobutyl 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and Di-tert-butyl 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

3,5-Dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrosophenyl)pyridine and Dichlorobis[3,5-dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)pyridine]copper(II)

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