132194-65-1

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid,2-[[2-(2-aminoethoxy)ethoxy]methyl]-4- (2,3-dichlorophenyl)-1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester,(4R)-
• CAS NO: 132194-65-1
• Molecular Weight: 487.38
• Mol File: 132194-65-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid,2-[[2-(2-aminoethoxy)ethoxy]methyl]-4- (2,3-dichlorophenyl)-1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester,(4R)- (CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid,2-[[2-(2-aminoethoxy)ethoxy]methyl]-4- (2,3-dichlorophenyl)-1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester,(4R)- (132194-65-1)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid,2-[[2-(2-aminoethoxy)ethoxy]methyl]-4- (2,3-dichlorophenyl)-1,4-dihydro-6-methyl-,3-ethyl 5-methyl ester,(4R)- (132194-65-1)

Safety Data

• Hazardous Substances Data: 132194-65-1(Hazardous Substances Data)

Upstream product

• 191285-83-3 (+)-2-{[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-6-methyl-1,4-dihydropyridine-5-carboxylic acid 
• 112641-19-7 Ethyl 4-(2-(2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy)ethoxy)-3-oxobutanoate 
• 75001-08-0 2-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}isoindole-1,3-dione 
• 75001-09-1 2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)acetic acid 
• 5197-62-6 2-[2-(chloroethoxy)ethoxy]ethanol 
• 191285-85-5 3-ethyl-5-methyl-(+)-{[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 186581-53-3 diazomethane 
• 191285-77-5 (+)-2-[(2-(2-aminoethoxy)ethoxy)methyl]-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-6-methyl-1,4-dihydropyridine-5-carboxylic acid 
• 191285-70-8 5-(2-cyanoethyl)-3-ethyl-(+/-)-2-{[2-(2-phthalimidoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 191285-72-0 3-ethyl-5-(2-trimethylsilylethyl)-(+/-)-2-{[2-(2-phthalimidoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 191285-80-0 3-ethyl-5-(2-trimethylsilylethyl)-(+/-)-2-{[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 191285-79-7 3-ethyl-5-(2-trimethylsilylethyl)-(+/-)-2-{[2-(2-aminoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 

Relevant articles and documents

Synthesis of two optically active calcium channel antagonists labelled with carbon-11 for in vivo cardiac PET imaging

(±)-S11568 (1, 3-ethyl-5-methyl-(±)-2-[(2-(2-aminoethoxy)ethoxy)methyl]-4-(2,3 -dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5- dicarboxylate), has an in vitro profile of high potency and of high selectivity for the low-voltage dependent L-type calcium channel. In in vitro binding studies, it displaced specifically bound (-)-[3H]PN 200-110 (isradipine (2), the reference molecule for in vitro studies) from cardiac and vascular smooth muscle preparations with potencies of 5.6 and 51 nM, respectively. It also appears as a pure pharmacological antagonist acting at a single channel L-type and free of any interaction at the benzothiazepine binding site such as amlodipine (3). Both enantiomers of S11568 have in vitro activities, the dextro isomer S12967 ((±)-1) being 6 to 18-fold less potent than the levo one S12968 ((-)-1). Two couples of optically active labelling precursors of S11568, ((-)-10/(+)-10 and (-)-14/(+)-14) have been synthesized using a modified Hantzsch's dihydropyridine synthesis. In both cases, the enantiomers were separated by preparative chiral HPLC. They both have been independently labelled with carbon-11, using [11C]diazomethane or [11C]iodomethane to give multimilliCurie quantities of (-)-1 (S12968) and (+)-1 (S12967) with high specific activities (500-1000 mCi/μmol, 18.5-37.0 GBq/μmol). Both enantiomers appear suitable for PET experiments: their myocardial concentration increases after a bolus injection to reach a maximum in 2 min and then remains on a plateau with a slight downslope while the blood concentration falls rapidly. Myocardial uptake was threefold higher than lung uptake, leading to a good contrast on PET images. The present preliminary biological results obtained in Beagle dogs showed that both enantiomers have similar myocardisk kinetics and in vivo affinity for the left ventricular myocardium.

1,4-dihydropyridine compounds

Compounds of general formula I: STR1 in which: Ar represents a phenyl radical optionally containing one to five identical or different substituents, representing a halogen atom, an alkoxy radical containing 1 to 4 carbon atoms, an alkylthio radical containing 1 to 4 carbon atoms, a trihalomethyl radical or a methylenedioxy radical, Y, Z, Y1, Z1, W, V, U, m, n, R1, R2 are as defined in the specification. The compounds are used as calcium modulators.