116324-79-9

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 4-(2,6-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, dimethyl ester
• CAS NO: 116324-79-9
• Molecular Formula: C17H17Cl2NO4
• Molecular Weight: 370.232
• Mol File: 116324-79-9.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 4-(2,6-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 4-(2,6-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, dimethyl ester(116324-79-9)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 4-(2,6-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, dimethyl ester(116324-79-9)

Safety Data

• Hazardous Substances Data: 116324-79-9(Hazardous Substances Data)

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 

Relevant articles and documents

Conformational dynamics of 4-aryl-1,4-dihydropyridine calcium channel antagonists. 1. Quantitation of C4-C1' bond rotational barriers

The solution state dynamics of six substituted 4-aryl-1,4- dihydropyridine calcium channel antagonist analogs were studied using saturation transfer, difference NOE and variable temperature NMR spectroscopy. Thermodynamic activation parameters for aryl ring rotation were determined for all six compounds from linear Eyring plots which span four orders of magnitude. The barrier to rotation about the ring juncture was also calculated at the AM1 level and these calculations correctly predict the general magnitude, though not the specific barriers, to rotation. The asymmetrically substituted compound, 1,4-dihydro-2,6-dimethyl- 4-(2'-chloro-6'-methylphenyl)-3,5-pyridine-dicarboxylic acid dimethyl ester (2a), showed a rotameric preference of 17:1 by NMR for having the aryl methyl group syn to the C4H of the dihydropyridine ring; AM1 correctly predicts this preference but overestimates its magnitude. In the crystal state, the rotameric ratio appears to be nearer 1:1.

PROCESS FOR THE PREPARATION OF 1,4-DIHYDROPYRIDINES AND NOVEL 1,4-DIHYDROPYRIDINES USEFUL AS THERAPEUTIC AGENTS

The present invention provides a process for the preparation of 1,4-dihydropyridines of the formula (1), wherein R1 is H, NO2, Cl, OAc, OH, R2 is H, NO2, Cl, -O-CH2-O-, OMe, OAc, OEt, OH, R3 is H, NO2, Cl, N(Me)2, -O- CH2 -O-, OMe, OAc, OH, R4 is H, OMe, OAc, OH, R5 is H, Cl, I, and R6 and R7 are either methyl, ethyl or both by preparing a mixture of an aromatic aldehyde, alkyl acetoacetate and a source of ammonia, adsorbing the prepared mixture and adsorbent till adsorbent becomes free flowing, heating the material so obtained under microwave irradiation, cooling the reaction mixture and recovering the compound of formula (1). The present invention also relates to novel 1,4-dihydropyridines with cardiovascular activity.

1,4-Dihydropyridine antagonist activities at the calcium channel: A quantitative structure-activity relationship approach

The effect of 46 1,4-dihydropyridine-type calcium channel antagonists on the tonic contractile response of longitudinal muscle strips of guinea pig ileum was determined. 2,6-Dimethyl-3,5-dicarbomethoxy-4-phenyl-1,4-dihydropyridine (13) and 13 ortho-, 15 meta-, and seven para-monosubstituted and 10 polysubstituted aromatic derivatives of 13 were studied. The pharmacological activities of the monosubstituted derivatives were best correlated by eq 10, log 1/C = 0.68π + 2.50σ(m) - 0.47L(meta) - 3.40B1(para) + 11.31, which had a correlation coefficient of 0.89. The full data set was best correlated by eq 11, log 1/C = 0.62π + 1.96σ(m) - 0.44L(meta) - 3.26B1(para) - 1.51L(meta) + 14.23, which had a correlation coefficient of 0.90. Equations of similar form but involving an ortho steric term were found to correlate the radioligand binding data for this class of compounds.