5-(3-Phenyl-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate | 215120-03-9

• 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-(3-Phenyl-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 5-O-(2-cyanoethyl) 3-O-(3-phenylprop-2-enyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 215120-03-9
• 化学式: C₂₅H₂₁ClN₂O₄
• 分子量: 448.906
• InChiKey: LSSNWVIREIWAFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(3-Phenyl-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 在 甲醇 、 sodium hydroxide 作用下， 生成 4-(3-Chlorophenyl)-5-(3-phenylprop-2-enoxycarbonyl)-1,4-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives

  摘要：

  A structure-activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.051
• 作为产物：
  描述：

  (2-cyanoethyl) propiolate 、 propynoic acid cinnamyl ester 、 3-氯苯甲醛 在 ammonium acetate 作用下， 以 异丙醇 为溶剂， 生成 5-(3-Phenyl-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives

  摘要：

  A structure-activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.051

文献信息

• Dihydropyridine derivative
  申请人：Ajinomoto Co., Inc.

  公开号：US06995179B2

  公开（公告）日：2006-02-07

  Dihydropyridine derivatives of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an activity of selectively inhibiting the action of N-type calcium channel. They are used as remedies for various diseases relating to the N-type calcium channel such as encephalopathies caused by the ischemia in the acute phase after the onset of cerebral infarction, cerebral hemorrhage or the like, Alzheimer's disease, etc.

  以下公式的二氢吡啶衍生物、其类似物和药学上可接受的盐具有选择性抑制N型钙通道作用的活性。它们被用作治疗与N型钙通道相关的各种疾病，如脑梗死、脑出血等急性期缺血引起的脑病，阿尔茨海默病等。