74936-72-4

Basic information

• Product Name: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester
• Synonyms: 2,6-DIMETHYL-5-METHOXY CARBONYL-4-(3-NITRO-PHENYL)-1,4-DIHYDROPYRIDINE-3-CARBOXYLIC ACID;1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester;Lercanidipine mainring;rac-1,4-Dihydro-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic Acid;1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-methyl ester;Methyl hydrogen 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate;2,6-DiMethyl-5-Methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydorpyridine-3-carboxylic acid;1,4-Dihydro-2,6-diMethyl-4-(3-nitrophenyl)-3,5-pyr
• CAS NO: 74936-72-4
• Molecular Formula: C₁₆H₁₆N₂O₆
• Molecular Weight: 332.31
• EINECS: 278-034-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycle-Pyridine series
• Mol File: 74936-72-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 200-202?C
• Boiling Point: 505 °C at 760 mmHg
• Flash Point: 259.2 °C
• Appearance: /
• Density: 1.345 g/cm³
• Vapor Pressure: 5.1E-11mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly), Methanol (Slightly, Heated)
• PKA: 1.66±0.70(Predicted)
• CAS DataBase Reference: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester(74936-72-4)
• EPA Substance Registry System: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester(74936-72-4)

Safety Data

• Hazardous Substances Data: 74936-72-4(Hazardous Substances Data)

Usage

Description

1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester, also known as Nicardipine USP Related Compound A, is a 1,4-dihydropyridine derivative with a light-yellow solid appearance. It is characterized by its chemical structure that includes a dihydropyridine ring with methyl groups at the 2 and 6 positions, a nitrophenyl group at the 4 position, and a methyl ester group attached to the 3-carboxylic acid.

Uses

Used in Pharmaceutical Industry:
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester is used as an active pharmaceutical ingredient for the prevention and therapy of atherosclerotic degradation of arterial walls. Its application is based on its ability to help maintain the integrity and function of the arterial walls, thus preventing the hardening and narrowing of the arteries, which can lead to various cardiovascular diseases.
Used in Cardiovascular Applications:
In the field of cardiology, 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester is utilized as a therapeutic agent for treating atherosclerosis. 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester works by reducing the degradation of arterial walls, which is a key factor in the development of atherosclerosis. By preventing this degradation, the compound helps to maintain healthy blood flow and reduce the risk of heart attacks and strokes.
Chemical Properties:
1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl Ester is a light-yellow solid, which indicates its stability and suitability for use in various pharmaceutical formulations. Its chemical properties, including its dihydropyridine structure and functional groups, contribute to its effectiveness in treating atherosclerotic conditions.

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)

Upstream product

• 75130-24-4 2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester 
• 39562-70-4 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester 
• 55985-32-5 Nicardipine 
• 119065-61-1 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-piperidin-3-yl) ester 5-methyl ester 
• 99-61-6 3-nitro-benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 22886-02-8 (1S)-2-ethoxy-1-methyl-2-oxoethyl 3-oxobutanoate 
• 80612-98-2 aminocrotonic acid methyl ester 
• 173407-10-8 isobutyl (R)-(+)-lactate acetoacetate 
• 21881-77-6 m-nifedipine 
• 7440-44-0 pyrographite 
• 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 
• 39562-17-9 methyl 2-(3-nitrophenylmethylene)acetoacetate 

Downstream Products

• 85677-95-8 2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 117280-67-8 8-[1,4-Dihydro-2,6-dimethyl-5methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carbonyl]-2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione 
• 134028-03-8 C₁₆H₁₆N₂O₆*C₁₉H₂₂N₂O 
• 1233222-22-4 C₂₁H₂₀N₂O₇ 
• 171352-81-1 C₂₄H₂₂N₂O₈ 
• 1233222-25-7 C₂₄H₂₃ClN₂O₆ 
• 1233222-24-6 C₂₅H₂₄N₂O₆ 
• 1233222-31-5 C₂₅H₂₆N₂O₇ 
• 119009-03-9 C₂₅H₂₄N₂O₆ 
• 1233222-28-0 C₂₆H₂₈N₂O₆ 
• 1233222-32-6 C₂₉H₂₆N₂O₆ 
• 1233222-29-1 C₂₇H₃₀N₂O₇ 
• 1233222-26-8 C₂₄H₂₃ClN₂O₇ 
• 1233222-27-9 C₂₆H₂₈N₂O₆ 

Relevant articles and documents

Preparation method of benidipine hydrochloride

The invention belongs to the field of chemical synthesis of drugs, and particularly relates to a preparation method of a hypotensive drug benidipine hydrochloride. The method comprises the following steps: carrying out a Knoevenagel reaction, a Michael addition reaction, cyclization and hydrolysis on starting raw materials 3-nitrobenzaldehyde and methyl acetoacetate in the presence of a catalyst, reacting with thionyl chloride, directly reacting with 1-benzyl-3-hydroxypiperidine, and refining to obtain the benidipine hydrochloride. The benidipine hydrochloride obtained by adopting the preparation method of the benidipine hydrochloride is high in purity, column chromatography isolation is not needed, and the HPLC purity of the product is 99.5% or above. The yield of the obtained benidipine hydrochloride is relatively high and can reach 68% or above.

Preparation method for 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester

The invention relates to a preparation method for an important intermediate of dihydropyridine hypotensive drugs, in particular to a preparation method for 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester. The problems of severe reaction conditions, long reaction time, more by-products and bad purity in the existing preparation method for 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester are solved. The preparation method comprises the steps that lipase and 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate are added in an aqueous solution/organic solvent mixed system and react, and a mixture is obtained through the reaction; the organic solvent is removed, NaOH aqueous solution is added, and powder is obtained through suction filtration, stirring, suction filtration and recrystallization one after another, wherein the powder is 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester. The preparation method for 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester is applied to the field of the dihydropyridine hypotensive drugs.

Design, synthesis, in Silico and in vitro studies of substituted 1, 2, 3, 4-Tetrahydro pyrimidine phosphorus derivatives

Molecular docking studies of the designed two series (4a-l, 6a-l, 9 and 10) of novel substituted phosphorylated 1, 4-dihydropyridine and 1,2,3,4-Tetrahydropyrimidine derivatives against the drug targets of DHFR from Bacillus cereus, LpxC from Pseudomonas aeruginosa, IDH from E. coli and MurB from Staphylococcus aureus were encouraged for their synthesis. These compounds were synthesized from substituted aromatic aldehydes, thiourea/urea and ethyl acetoacetate in the presence of polyphosphoric acid (PPA). These were further phosphorylated with diethyl (2-chloroethoxy) methyl phosphonate to get the desired products. In vitro anti-bacterial activity against the specified bacterial strains related to docked protein exhibited good inhibitory activity at different dose concentrations. Quantitative Structure Activity Relationship (QSAR) descriptors of the designed structures have demonstrated their satisfactory drug like properties. The results from Molecular Docking, QSAR descriptors and in vitro anti-bacterial activities led to the identification of safer and potential antibacterial agents of the title compounds screened. Compounds 4a, 4d, 4i, 6a, 6d, 9 and 10 were found to be potent antibacterial agents.