76093-34-0

Basic information

• Product Name: (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester
• Synonyms: (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester;3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-diMethyl-4-(3-nitrophenyl)-, 3-Methyl ester, (4S)-;(S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl es
• CAS NO: 76093-34-0
• Molecular Formula: C₁₆H₁₆N₂O₆
• Molecular Weight: 332.32
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Dihydropyridine
• Mol File: 76093-34-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 505°C at 760 mmHg
• Flash Point: 259.2°C
• Appearance: /
• Density: 1.345g/cm³
• Vapor Pressure: 5.1E-11mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.66±0.70(Predicted)
• CAS DataBase Reference: (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester(76093-34-0)
• EPA Substance Registry System: (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester(76093-34-0)

Safety Data

• Hazardous Substances Data: 76093-34-0(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Solid

Uses

1,4-Dihydropyridine derivative used in the prevention and therapy of atherosclerotic degradation of arterial walls

InChI:InChI=1/C16H16N2O6/c1-8-12(15(19)20)14(13(9(2)17-8)16(21)24-3)10-5-4-6-11(7-10)18(22)23/h4-7,14,17H,1-3H3,(H,19,20)/t14-/m0/s1

Upstream product

• 76093-32-8 (4S)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid 
• 143167-32-2 2-cyanoethyl (R)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylate 
• 152253-28-6 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-methanesulfonyl-ethyl) ester 5-methyl ester 
• 76093-31-7 1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid 
• 152375-53-6 (4R)-1,4-dihydro-3-(2-cyanoethyl)oxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid 
• 152253-24-2 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid mono-(2-methanesulfonyl-ethyl) ester 
• 134028-03-8 C₁₆H₁₆N₂O₆*C₁₉H₂₂N₂O 
• 99-61-6 3-nitro-benzaldehyde 
• 21881-77-6 m-nifedipine 
• 74936-72-4 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid 
• 88712-56-5 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride 
• 102993-38-4 2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate 
• 75130-24-4 2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester 
• 76093-31-7 1-Ethoxymethyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester 

Downstream Products

• 55985-32-5 (-)-nicardipine 
• 55985-32-5 (+)-nicardipine 
• 119746-76-8 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-{[(R)-1-(2,3-dihydro-benzo[1,4]dioxin-2-yl)methyl]-methyl-amino}-ethyl) ester 5-methyl ester 
• 119746-74-6 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-{[(S)-1-(2,3-dihydro-benzo[1,4]dioxin-2-yl)methyl]-methyl-amino}-ethyl) ester 5-methyl ester 
• 88712-56-5 methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 105979-17-7 benidipine 
• 119065-61-1 (R,S)-Benidipine 
• 104757-55-3 (3R)-1-benzyl-3-pyrrolidinyl methyl (4R)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 104757-54-2 (+)-(3'S,4S)-3-(1'-benzyl-3'-pyrrolidinyl) methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 77940-88-6 BAY 3629 
• 89226-75-5 (-)-manidipine dihydrochloride 
• 134028-04-9 (4S)-(+)-2-<4-(4-Benzhydryl-1-piperazinyl)phenyl>ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 195065-58-8 3-Iodopropyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylate 
• 195065-71-5 3-(3-pyridyl)propyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylate 

Relevant articles and documents

Barnidipine hydrochloride compound and preparation method thereof

The invention discloses a barnidipine hydrochloride compound and a preparation method thereof. The preparation method comprises the following steps: (1) using 3-hydroxypropionitrile to react with diketene, to obtain an intermediate 1; (2) enabling the intermediate 1 to react with m-nitrobenzaldehyde and Beta-amino methyl crotonate, to obtain an intermediate 2; (3) enabling the intermediate 2 to behydrolyzed by strong base, to obtain an intermediate 3; (4) enabling the intermediate 3 to be resolved by chiral organic base, to obtain an intermediate 4; (5) enabling the intermediate 4 to react with thionyl chloride, (S)-1-benzyl-3-pyrrolidinol, and HCI ethanol solution, to obtain a crude product of barnidipine hydrochloride; and (6) performing ethyl alcohol pulping and refining, and ethyl alcohol recrystallization on the crude product of the barnidipine hydrochloride, to obtain the barnidipine hydrochloride.

1,4-dihydropyridine-3,5-dicarboxylate Derivatives And Preparation And Use Thereof

The present invention relates to a 1,4-dihydropyridine-3,5-dicarboxylate compound of general compound (I), a process for preparing the same, a use thereof for the manufacture of a medicament for treating and/or preventing kidney injury, cardiovascular diseases and/or endocrine diseases, as well as a pharmaceutical composition and a pharmaceutical formulation containing said compounds, wherein the definitions of R1, R2, R3, R4, R5, R6, R7, R8, m, n1, n2, p and q are the same as those defined in the description.

Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

An efficient total synthesis of (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in high optical purities is reported. The useful step is the resolution of racemic 2, 6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid by using commercially available Cinchona alkaloids cinchonidine and quinidine as the resolving agents. Under the optimum conditions, the optical purities for R- and S-enantiomers are extremely high (ee >99.5%). The further dihydropyridine receptor binding activity assay shows that the S-enantiomer is more potent than R-enantiomer both in rat cardiac (approximately 19 times) and cerebral cortex membrane (12 times).