[1-[3,3-Diphenylpropyl(methyl)amino]-2-methylpropan-2-yl] 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate | 210579-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-[3,3-Diphenylpropyl(methyl)amino]-2-methylpropan-2-yl] 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
• CAS: 210579-45-6
• 化学式: C₃₁H₃₄N₂O₅
• 分子量: 514.621
• InChiKey: BCYDMCYQBTZFDU-UHFFFAOYSA-N

物化性质

• 沸点：
  645.6±55.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)
• 溶解度：
  溶于DCM、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-氨基巴豆酸甲酯 、 [1-[3,3-Diphenylpropyl(methyl)amino]-2-methylpropan-2-yl] 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate 以 异丙醇 为溶剂， 生成 乐卡地平
  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：

  N-甲基-3,3-二苯基丙胺 在 盐酸 作用下， 以 氯仿 、 甲苯 、 xylene 为溶剂， 反应 10.5h， 生成 [1-[3,3-Diphenylpropyl(methyl)amino]-2-methylpropan-2-yl] 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate
  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

• Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity
  作者：Amedeo Leonardi、Gianni Motta、Renzo Pennini、Rodolfo Testa、Giorgio Sironi、Alberto Catto、Alberto Cerri、Marco Zappa、Giorgio Bianchi、Dante Nardi

  DOI：10.1016/s0223-5234(98)80015-9

  日期：1998.6

  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.