5-O-(2-cyanoethyl) 3-O-(3-phenylprop-2-enyl) 4-(3-chlorophenyl)-2-cyano-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate | 215119-92-9

• 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: 5-O-(2-cyanoethyl) 3-O-(3-phenylprop-2-enyl) 4-(3-chlorophenyl)-2-cyano-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 215119-92-9
• 化学式: C₂₇H₂₂ClN₃O₄
• 分子量: 487.942
• InChiKey: FUIZNBXYPXOVLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-O-(2-cyanoethyl) 3-O-(3-phenylprop-2-enyl) 4-(3-chlorophenyl)-2-cyano-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 在 甲醇 、 sodium hydroxide 、 水 作用下， 生成 4-(3-Chlorophenyl)-6-cyano-2-methyl-5-(3-phenylprop-2-enoxycarbonyl)-1,4-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  The structure–activity relationship study on 2-, 5-, and 6-position of the water soluble 1,4-dihydropyridine derivatives blocking N-type calcium channels

  摘要：

  In order to find an injectable and selective N-type calcium channel blocker, we have performed the structure-activity relationship (SAR) study on the 2-, 5-, and 6-position of 1,4-dihydropyridine-3-carboxylate derivative APJ2708 (2), which is a derivative of Cilnidipine and has L/N-type calcium channel dual inhibitory activities. As a consequence of the optimization, 6-dimethylacetal derivative 7 was found to have an effective inhibitory activity against N-type calcium channels with more than 170-fold lower activity for L-type channel compared to that of APJ2708. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.096
• 作为产物：
  描述：

  3-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine 3,5-dicarboxylate 在 羟胺 、 sodium acetate 、 溶剂黄146 、 乙酸酐 作用下， 生成 5-O-(2-cyanoethyl) 3-O-(3-phenylprop-2-enyl) 4-(3-chlorophenyl)-2-cyano-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  The structure–activity relationship study on 2-, 5-, and 6-position of the water soluble 1,4-dihydropyridine derivatives blocking N-type calcium channels

  摘要：

  In order to find an injectable and selective N-type calcium channel blocker, we have performed the structure-activity relationship (SAR) study on the 2-, 5-, and 6-position of 1,4-dihydropyridine-3-carboxylate derivative APJ2708 (2), which is a derivative of Cilnidipine and has L/N-type calcium channel dual inhibitory activities. As a consequence of the optimization, 6-dimethylacetal derivative 7 was found to have an effective inhibitory activity against N-type calcium channels with more than 170-fold lower activity for L-type channel compared to that of APJ2708. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.096