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1,4-dihydropyridine compound including acetoacetanilide structure and preparation method thereof

A technology of acetoacetanilide and dihydropyridine, applied in the field 1, can solve problems such as difficult derivatization, unfavorable molecular diversity research, cumbersome synthesis methods, etc., and achieve good drug dynamics and kinetic properties, good drug use prospects, The effect of the simple synthesis method

Inactive Publication Date: 2012-01-04
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] After research and analysis, the above-mentioned 1,4-dihydropyridine compounds still have problems such as single reaction site, difficult derivatization, poor selectivity, cumbersome synthesis methods, and unfavorable research on molecular diversity.

Method used

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  • 1,4-dihydropyridine compound including acetoacetanilide structure and preparation method thereof
  • 1,4-dihydropyridine compound including acetoacetanilide structure and preparation method thereof
  • 1,4-dihydropyridine compound including acetoacetanilide structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of 2,6-dimethyl-3,5-[N,N-diphenyl]dicarboxamido-1,4-dihydropyridine

[0029] Dissolve 1.77g (0.01mol) of 2,4-dimethylacetoacetanilide in 40mL of ethanol, add 1.40g (0.01mol) of hexamethylenetetramine and 1.54g (0.02mol) of ammonium acetate to the solution 10mL aqueous solution, heated at 55-70°C for 1.5h. Most of the solvent was removed by rotary evaporation, and a large amount of light yellow solid was precipitated, which was cooled to room temperature and then suction filtered. The precipitate was first washed 3 times with 2 mL of 50% (V / V) methanol-water solution, then washed 3 times with 5 mL of water, and dried to obtain 1.53 g of light yellow solid powder with a yield of 83.3%. The melting point of the product is 224-226°C. The purity of the product analyzed by HPLC normalization method was 99.5%.

[0030] The structural analysis is as follows:

[0031] 1 H-NMR (500MHz, DMSO-d 6 )δ: 2.02(s, 6H, 2×CH 3 ), 3.41 (s, 2H, CH 2 ), 6.98~7.64 (m, 10H, 2×...

Embodiment 2

[0034] The synthesis of 2,6-dimethyl-3,5-[N,N-bis(2,5-dimethoxy-4-chloro)phenyl]dicarboxamido-1,4-dihydropyridine will 2.72g (0.01mol) of 2,5-dimethoxy-4-chloroacetoacetanilide was dissolved in 40mL of isopropanol, and 1.44mL (0.02mol) of 37-40% formaldehyde solution and 5mL of dissolved 1.54g (0.02mol) ammonium acetate aqueous solution was heated at 55-70°C for 2h. Most of the solvent was evaporated by rotary evaporation, and a large amount of yellow solid precipitated out, which was cooled to room temperature and suction filtered. The precipitate was washed 3 times with 2 mL of 50% (V / V) methanol-water solution and then 3 times with 5 mL of water. After drying, 1.96 g of light yellow solid powder was obtained with a yield of 73.3%. The melting point of the product is 239-241°C. The purity of the product analyzed by HPLC normalization method was 98.5%.

[0035] The structural analysis is as follows:

[0036] 1 H-NMR (500MHz, CDCl 3 )δ: 2.43(s, 6H, 2×CH 3 ), 3.65(s, 6H,...

Embodiment 3

[0039] Synthesis of 2,6-Dimethyl-3,5-[N,N-bis(potassium p-sulfonate)phenyl]dicarboxamido-1,4-dihydropyridine

[0040] Dissolve 2.95g (0.01mol) of potassium p-sulfonate acetoacetanilide in 40mL of 50% (V / V) methanol-water, add 2.80g (0.02mol) of hexamethylenetetramine and 3.08g of (0.04mol) 10mL aqueous solution of ammonium acetate, heated at 55-70°C for 2.5h. Most of the solvent was removed by rotary evaporation, and a large amount of light yellow solid was precipitated, which was cooled to room temperature and then suction filtered. The precipitate was first washed 5 times with 2 mL of 50% (V / V) methanol-water solution, and dried to obtain 2.43 g of light yellow solid powder with a yield of 83.4%. The purity of the product analyzed by HPLC normalization method was 98.7%.

[0041] The structural analysis is as follows:

[0042] 1 H-NMR (500MHz, DMSO-d 6 )δ: 2.03(s, 6H, 2×CH 3 ), 3.42 (s, 2H, CH 2 ), 7.48~7.61 (m, 8H, 2×PhH), 7.84 (s, H, NH), 9.13 (s, 2H, 2×NH).

[0043] ...

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Abstract

The invention belongs to the field of 1,4-dihydropyridine compounds and in particular relates to a 1,4-dihydropyridine compound including an acetoacetanilide structure and a preparation method thereof. The 1,4-dihydropyridine compound is shown as a structural general formula in the specification. The preparation method comprises the following steps of: taking an acetoacetanilide derivative, ammonium acetate, hexamine or formaldehyde as raw materials, carrying out condensation reaction under a heating condition; and obtaining an objective product after purifying. The method for synthesizing the compound in the invention is simple and rapid. A lot of compound libraries can be synthesized in a short period. The method is applied to researching the molecular diversity of the compound.

Description

technical field [0001] The invention belongs to the field of 1,4-dihydropyridine compounds, in particular to a 1,4-dihydropyridine compound containing an acetoacetanilide structure and a preparation method thereof. Background technique [0002] 1,4-Dihydropyridine compounds have a wide range of biological functions, and have broad application prospects in medicine and biology. It is widely used clinically to treat cardiovascular diseases such as angina pectoris, hypertension, arrhythmia, and heart failure (K Taya, Y Watanabe, H Kobayashi, et al. Physiol. Behav. 2000, 70: 19-25.). As a class of high-efficiency calcium ion antagonists that can selectively expand small artery smooth muscle, reduce peripheral resistance, lower blood pressure, and reduce myocardial oxygen consumption [a) R D Anana, E E Knaus.Arch.Pharm.1996, 329 (8- 9): 408~412; b) K Chandra Mohan, K Ravikumar, M M Shetty, et al.Z.Kristallogr.2003, 218(1): 46~55.; c) X Q Li, W Cao, A G Zeng, et al. al.Clin Exp ...

Claims

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Application Information

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IPC IPC(8): C07D211/90
Inventor 李方实陈学军
Owner NANJING UNIV OF TECH
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