3-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine 3,5-dicarboxylate | 215119-91-8

• 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: 3-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine 3,5-dicarboxylate
• 英文别名: 5-O-(2-cyanoethyl) 3-O-(3-phenylprop-2-enyl) 4-(3-chlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 215119-91-8
• 化学式: C₂₇H₂₃ClN₂O₅
• 分子量: 490.943
• InChiKey: AGFKOCZXCUXOAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,4-dihydropyridinedicarboxylic acid 2-cyanoethyl ester 5-cinnamyl ester 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 生成 3-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-formyl-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

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。
• The structure–activity relationship study on 2-, 5-, and 6-position of the water soluble 1,4-dihydropyridine derivatives blocking N-type calcium channels
  作者：Takashi Yamamoto、Seiji Niwa、Seiji Ohno、Munetaka Tokumasu、Yoko Masuzawa、Chika Nakanishi、Akira Nakajo、Tomoyuki Onishi、Hajime Koganei、Shin-ichi Fujita、Tomoko Takeda、Morikazu Kito、Yukitsugu Ono、Yuki Saitou、Akira Takahara、Seinosuke Iwata、Masataka Shoji

  DOI：10.1016/j.bmcl.2008.07.096

  日期：2008.9

  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.