4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-methyl ester | 100427-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-methyl ester
• 英文别名: 5-O-(2-chloroethyl) 3-O-methyl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 100427-01-8
• 化学式: C₁₈H₁₈ClN₃O₅
• 分子量: 391.811
• InChiKey: JHXIPDLUJJVUBW-UHFFFAOYSA-N

物化性质

• 沸点：
  539.7±60.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-甲基-3,3-二苯基丙胺 、 4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-methyl ester 生成 4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-{2-[(3,3-diphenyl-propyl)-methyl-amino]-ethyl} ester 5-methyl ester
  参考文献：
  名称：

  Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

  摘要：

  A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenyl-propylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4-dihydropyridines binding site labelled by H-3-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375-lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80015-9
• 作为产物：
  描述：

  苯并二唑-4-甲醛 在 盐酸 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 181.0h， 生成 4-Benzo[1,2,5]oxadiazol-4-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-chloro-ethyl) ester 5-methyl ester
  参考文献：
  名称：

  Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

  摘要：

  A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenyl-propylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4-dihydropyridines binding site labelled by H-3-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375-lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80015-9

文献信息

• US4772621A
  申请人：——

  公开号：US4772621A

  公开（公告）日：1988-09-20
• US4705797A
  申请人：——

  公开号：US4705797A

  公开（公告）日：1987-11-10