74936-72-4

Usage

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

• 39562-70-4 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester 
• 55985-32-5 Nicardipine 
• 99-61-6 3-nitro-benzaldehyde 
• 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 
• 75-09-2 dichloromethane 
• 75130-24-4 2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester 
• 21881-77-6 m-nifedipine 
• 7440-44-0 pyrographite 
• 39562-20-4 MN-92019 
• 102993-38-4 2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate 
• 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 

Downstream Products

• 64603-72-1 SL 5721 
• 88712-56-5 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride 
• 85677-95-8 2-hydroxyethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 681816-63-7 2-(2-oxo-4,3a-dihydroimidazolidino[2,1-b]quinazolin-6-yloxy)ethyl-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 143092-98-2 ethyl 2-[N-[1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carbonyl]amino]benzoate 
• 114208-20-7 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(3-bromopropyl)-ester 
• 110980-12-6 Methyl 3-perfluorohexyl-propyl (-)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate 
• 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 
• 129511-32-6 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-phenylthiomethyl 5-methylester 
• 134028-03-8 C₁₆H₁₆N₂O₆*C₁₉H₂₂N₂O 
• 1233222-22-4 C₂₁H₂₀N₂O₇ 

Relevant academic research and scientific papers

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.

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.

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.

Process for synthesis of hydrochloric acid ramiah of lercanidipine (by machine translation)

The invention discloses a process for synthesizing hydrochloric acid ramiah of lercanidipine, its synthesis process comprises the following steps : (1) 3 -? Hydroxy-propionitrile (I) and (II) reaction of ketene dimer, to obtain compound (VI) ; (2) compound (III) with (VI) reaction between formaldehyde nitrobenzene, to obtain compound (VII) ; (3) compound (VII) with β-amino-crotonic acid ethyl ester (IV) reaction, to obtain compound (VIII) ; (4) by strong alkali hydrolysis of compound (VIII), to obtain compound (IX) ; (5) compound (IX) using chiral organic alkali splitting, to obtain compound (X) ;? (6) compound (X) with benzyl quick (V) reaction, to obtain compound (XI) ; (7) a solution of compound (XI) by adding hydrogen chloride, hydrochloric acid ramiah horizontal (XII) can be obtained. Synthetic process of this invention has the following several advantages : (1) mild reaction conditions, each step the product is easy to separate, purification, controllable quality ; (2) higher yield for each step, the used original helping material is easy to obtain, the total cost is low ; (3) do not need to be too column, is suitable for industrial production. (by machine translation)

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.

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.

1,4-DIHYDROPYRIDINE -3,5-DICARBOXYLATE DERIVATIVES, PREPARATION METHODS AND USES 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 characterization of impurities of barnidipine hydrochloride, an antihypertensive drug substance

Barnidipine hydrochloride is a long term dihydropyridine calcium channel blocker used for the treatment of hypertension. During the process development of barnidipine hydrochloride, four barnidipine impurities were detected by high-performance liquid chromatography (HPLC) with an ordinary column (Agilent ZORBAX Eclipse XDB-C18, 150 mm × 4.6 mm, 5 m). All these impurities were identified, synthesized, and subsequently characterized by their respective spectral data (MS, 1H-NMR, and 13C-NMR). The identification of these impurities should be useful for quality control in the manufacture of barnidipine.

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).

Synthesis and biological evaluation of novel hybrid chalcone derivatives as vasorelaxant agents

With the aim to further improve the vasorelaxant activities of chalcones, nine hybrid chalcone derivatives conjugated with nitric oxide (NO) donor or 1,4-dihydropyridyl (1,4-DHP) moiety were designed and synthesized based on molecular hybridization strategy. Their vasorelaxant activities were evaluated in aortic rings with endothelium pre-contracted with phenylephrine (PE). All of these compounds showed preferable vasorelaxant activities which were more potent than their parent compounds. Compounds 8c and 15c, the most potent compounds, would be promising structural templates for the development of novel vasorelaxant agents. Nine hybrid chalcone derivatives conjugated with nitric oxide (NO) donors or 1,4-dihydropyridyl moiety were designed, synthesized and biological evaluated for their vasorelaxant activities.