2,6-dimethyl-4-[3-(2,3-epoxypropoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester | 51336-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-dimethyl-4-[3-(2,3-epoxypropoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 2,6-dimethyl-4-[3-(oxiran-2-ylmethoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate；diethyl 2,6-dimethyl-4-[3-(oxiran-2-ylmethoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 51336-21-1
• 化学式: C₂₂H₂₇NO₆
• 分子量: 401.459
• InChiKey: AYQWKMNGJPRGKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-[3-(2,3-epoxypropoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 以72%的产率得到4-[3-(3-Chloro-2-hydroxy-propoxy)-phenyl]-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Microwave-assisted synthesis of antimicrobial dihydropyridines and tetrahydropyrimidin-2-ones: Novel compounds against aspergillosis

  摘要：

  Ten 4-aryl-1,4-dihydropyridine and three 4-aryl-1,2,3,4-tetrahydropyrimidin-2-one derivatives have been synthesized and examined for their activity against pathogenic strains of Aspergillus fumigatus and Candida albicans. Although none of the three compounds belonging to pyrimidin-2-one series showed any activity against two pathogens, two of the compounds of the dihydropyridine series, that is, diethyl 4-(methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate and dimethyl 4-(4-methoxy-phenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate, exhibited significant activity against A. fumigatus in disc diffusion, microbroth dilution and percent spore germination inhibition assays. The most active diethyl dihydropyridine derivative exhibited a MIC value of 2.92 mu g/disc in disc diffusion and 15.62 mu g/ml in microbroth dilution assays. The MIC90 value of the most active compound by percent germination inhibition assay Was found to be 15.62 mu g/ml. The diethyl dicarboxylate derivative of dihydropyridine also exhibited appreciable activity against C. albicans. The in vitro toxicity of the most active diethyl dihydropyridine derivative was evaluated using haemolytic assay, in which the Compound was found to be non-toxic to human erythrocytes even at a concentration of 625 mu g/ml. The standard drug amphotericin B exhibited 100% lysis of erythrocytes at a concentration almost 16 times less than the safer concentration of the most active dihydropyridine derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.014
• 作为产物：
  描述：

  间羟基苯甲醛 在 potassium carbonate 、 尿素 作用下， 以 乙醇 为溶剂， 生成 2,6-dimethyl-4-[3-(2,3-epoxypropoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Microwave-assisted synthesis of antimicrobial dihydropyridines and tetrahydropyrimidin-2-ones: Novel compounds against aspergillosis

  摘要：

  Ten 4-aryl-1,4-dihydropyridine and three 4-aryl-1,2,3,4-tetrahydropyrimidin-2-one derivatives have been synthesized and examined for their activity against pathogenic strains of Aspergillus fumigatus and Candida albicans. Although none of the three compounds belonging to pyrimidin-2-one series showed any activity against two pathogens, two of the compounds of the dihydropyridine series, that is, diethyl 4-(methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate and dimethyl 4-(4-methoxy-phenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate, exhibited significant activity against A. fumigatus in disc diffusion, microbroth dilution and percent spore germination inhibition assays. The most active diethyl dihydropyridine derivative exhibited a MIC value of 2.92 mu g/disc in disc diffusion and 15.62 mu g/ml in microbroth dilution assays. The MIC90 value of the most active compound by percent germination inhibition assay Was found to be 15.62 mu g/ml. The diethyl dicarboxylate derivative of dihydropyridine also exhibited appreciable activity against C. albicans. The in vitro toxicity of the most active diethyl dihydropyridine derivative was evaluated using haemolytic assay, in which the Compound was found to be non-toxic to human erythrocytes even at a concentration of 625 mu g/ml. The standard drug amphotericin B exhibited 100% lysis of erythrocytes at a concentration almost 16 times less than the safer concentration of the most active dihydropyridine derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.014

文献信息

• 1,4-Dihydropyridines
  申请人：Bayer Aktiengesellschaft

  公开号：US03959296A1

  公开（公告）日：1976-05-25

  Derivatives of 4-substituted phenyl 1,4-dihydropyridine 3,5-dicarboxylic acids substituted by lower alkyl groups in the 2- and 6-positions, are cardiovascular agents. The compounds, of which 2,6-dimethyl-4-[2-(diethylaminoethoxy)-phenyl]-1,4-dihydropyridine-3,5-dic arboxylic acid 3,5-diethyl ester is a typical example, can be prepared through condensation of a .beta.-dicarbonyl compound with an amine and an aldehyde, of an ylidene-.beta.-ketocarboxylic acid ester, with a .beta.-ketocarbonyl compound and an amine, of an aldehyde, an enamine and a .beta.-ketocarbonyl compound, or through elaboration of the substituent on the phenyl group.

  4-取代苯基1,4-二氢吡啶-3,5-二羧酸的衍生物，其在2-和6-位被较低的烷基取代，是心血管药物。这些化合物，其中2,6-二甲基-4-[2-(二乙氨基乙氧基)-苯基]-1,4-二氢吡啶-3,5-二羧酸3,5-二乙酯是一个典型的例子，可以通过将β-二羰基化合物与胺和醛、与一个叶基-β-酮羧酸酯、与一个β-酮羰基化合物和一个胺、与一个醛、一个烯胺和一个β-酮羰基化合物进行缩合，或通过对苯基上的取代基进行详细处理来制备。
• US3959296A
  申请人：——

  公开号：US3959296A

  公开（公告）日：1976-05-25
• US3968117A
  申请人：——

  公开号：US3968117A

  公开（公告）日：1976-07-06
• Microwave-assisted synthesis of antimicrobial dihydropyridines and tetrahydropyrimidin-2-ones: Novel compounds against aspergillosis
  作者：Anil K. Chhillar、Pragya Arya、Chandrani Mukherjee、Pankaj Kumar、Yogesh Yadav、Ajendra K. Sharma、Vibha Yadav、Jyotsana Gupta、Rajesh Dabur、Hirday N. Jha、Arthur C. Watterson、Virinder S. Parmar、Ashok K. Prasad、Gainda L. Sharma

  DOI：10.1016/j.bmc.2005.09.014

  日期：2006.2

  Ten 4-aryl-1,4-dihydropyridine and three 4-aryl-1,2,3,4-tetrahydropyrimidin-2-one derivatives have been synthesized and examined for their activity against pathogenic strains of Aspergillus fumigatus and Candida albicans. Although none of the three compounds belonging to pyrimidin-2-one series showed any activity against two pathogens, two of the compounds of the dihydropyridine series, that is, diethyl 4-(methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate and dimethyl 4-(4-methoxy-phenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate, exhibited significant activity against A. fumigatus in disc diffusion, microbroth dilution and percent spore germination inhibition assays. The most active diethyl dihydropyridine derivative exhibited a MIC value of 2.92 mu g/disc in disc diffusion and 15.62 mu g/ml in microbroth dilution assays. The MIC90 value of the most active compound by percent germination inhibition assay Was found to be 15.62 mu g/ml. The diethyl dicarboxylate derivative of dihydropyridine also exhibited appreciable activity against C. albicans. The in vitro toxicity of the most active diethyl dihydropyridine derivative was evaluated using haemolytic assay, in which the Compound was found to be non-toxic to human erythrocytes even at a concentration of 625 mu g/ml. The standard drug amphotericin B exhibited 100% lysis of erythrocytes at a concentration almost 16 times less than the safer concentration of the most active dihydropyridine derivative. (c) 2005 Elsevier Ltd. All rights reserved.