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

Description

(S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester is a 1,4-dihydropyridine derivative, a class of chemical compounds known for their diverse range of biological activities and potential therapeutic applications. This specific compound is characterized by its unique molecular structure, featuring a 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine core and a monomethyl ester functional group. Its stereochemistry is defined by the (S)-(+) configuration, which may contribute to its distinct properties and potential uses.

Uses

Used in Cardiovascular Applications:
(S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Monomethyl Ester is used as a therapeutic agent for the prevention and treatment of atherosclerotic degradation of arterial walls. Atherosclerosis is a chronic inflammatory disease characterized by the buildup of plaque in the arterial walls, leading to reduced blood flow and an increased risk of cardiovascular events such as heart attacks and strokes. This 1,4-dihydropyridine derivative may exert its beneficial effects through various mechanisms, including the modulation of vascular tone, inhibition of smooth muscle cell proliferation, and anti-inflammatory actions.
In the pharmaceutical industry, this compound may be further developed and optimized for its potential use in cardiovascular medications, targeting the prevention and treatment of atherosclerosis and related cardiovascular diseases. Its unique structure and stereochemistry may provide advantages over existing therapies, offering new opportunities for the management of cardiovascular health.

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

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

Downstream Products

• 1404063-61-1 (4R)-3-(1-benzyl-3-methylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 104757-53-1 [14C]-Barnidipine hydrochloride 
• 104713-77-1 (3R)-1-benzyl-3-pyrrolidinyl methyl (4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 195065-71-5 3-(3-pyridyl)propyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylate 
• 195065-58-8 3-Iodopropyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylate 
• 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 
• 89226-75-5 (-)-manidipine dihydrochloride 
• 77940-88-6 BAY 3629 
• 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 
• 104757-55-3 (3R)-1-benzyl-3-pyrrolidinyl methyl (4R)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride 
• 119065-61-1 (R,S)-Benidipine 
• 105979-17-7 benidipine 
• 88712-56-5 methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 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 

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).