methyl 2-(chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate | 1226851-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 2-(chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate
• CAS: 1226851-35-9
• 化学式: C₁₉H₁₆ClN₃O₂
• 分子量: 353.808
• InChiKey: FLUAOTJNABTFRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.01
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 生成 methyl (4S)-2-(chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate hydrochloride 、 methyl (4R)-2-(chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate hydrochloride
  参考文献：
  名称：

  Stereochemical Requirements for the Mineralocorticoid Receptor Antagonist Activity of Dihydropyridines

  摘要：

  A number of known 1,4-dihydropyridine CCBs were identified as having comparable potency to the steroidal MR antagonist eplerenone. Chiral resolution of mebudipine revealed that MR and CCB activity reside in opposite enantiomers. Small molecule X-ray crystal structures showed that the C4 stereochemistry of optimized selective MR analogues, e.g. 5, is consistent with MR-active mebudipine. Molecular modeling supports a binding pose consistent with that previously proposed for DHP diesters.

  DOI：

  10.1021/jm1002827
• 作为产物：
  描述：

  4-喹啉甲醛 、 3-氨基巴豆腈 、 4-氯乙酰乙酸甲酯 在 哌啶 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 40.0h， 生成 methyl 2-(chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Stereochemical Requirements for the Mineralocorticoid Receptor Antagonist Activity of Dihydropyridines

  摘要：

  A number of known 1,4-dihydropyridine CCBs were identified as having comparable potency to the steroidal MR antagonist eplerenone. Chiral resolution of mebudipine revealed that MR and CCB activity reside in opposite enantiomers. Small molecule X-ray crystal structures showed that the C4 stereochemistry of optimized selective MR analogues, e.g. 5, is consistent with MR-active mebudipine. Molecular modeling supports a binding pose consistent with that previously proposed for DHP diesters.

  DOI：

  10.1021/jm1002827

文献信息

• Stereochemical Requirements for the Mineralocorticoid Receptor Antagonist Activity of Dihydropyridines
  作者：Graciela B. Arhancet、Scott S. Woodard、Jessica D. Dietz、Danny J. Garland、Grace M. Wagner、Kaliappan Iyanar、Joe T. Collins、James R. Blinn、Randal E. Numann、Xiao Hu、Horng-Chih Huang

  DOI：10.1021/jm1002827

  日期：2010.5.27

  A number of known 1,4-dihydropyridine CCBs were identified as having comparable potency to the steroidal MR antagonist eplerenone. Chiral resolution of mebudipine revealed that MR and CCB activity reside in opposite enantiomers. Small molecule X-ray crystal structures showed that the C4 stereochemistry of optimized selective MR analogues, e.g. 5, is consistent with MR-active mebudipine. Molecular modeling supports a binding pose consistent with that previously proposed for DHP diesters.