(-)-Mono-N-Desisopropyldisopyramide | 77494-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-Mono-N-Desisopropyldisopyramide
• 英文别名: (2R)-4-(isopropylamino)-2-phenyl-2-(2-pyridyl)butyramide；(R)-Monodes(isopropyl)disopyramide；(2R)-2-phenyl-4-(propan-2-ylamino)-2-pyridin-2-ylbutanamide
• CAS: 77494-40-7
• 化学式: C₁₈H₂₃N₃O
• 分子量: 297.4
• InChiKey: UWNSWIXIVDMCHZ-GOSISDBHSA-N

物化性质

• 沸点：
  504.4±50.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  达舒平 在 potassium carbonate 、 间氯过氧苯甲酸 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 (-)-Mono-N-Desisopropyldisopyramide
  参考文献：
  名称：

  Synthesis and anticholinergic properties of the enantiomers of 4-(isopropylamino)-2-(2-pyridyl)-2-phenylbutyramide, the mono-N-dealkylated metabolite of disopyramide

  摘要：

  The 2R and 2S enantiomers of 4-isopropyl-2-(2-pyridyl)-2-phenylbutyramide [(2R)-2 and (2S)-2] were prepared from the respective 2R and 2S enantiomers of disopyramide [(2R)-1 and (2S)-1] by oxidation with peracid, Cope elimination, and subsequent zinc/HCl reduction of the resulting hydroxylamines (2R)-3 and (2S)-3. The enantiomers were tested as antagonists to the contraction of guinea pig ileum longitudinal muscle produced in response to electrically stimulated release of acetylcholine. The enantiomers showed IC50 values of 5.0 X 10(-6) and 14 X 10(-6) M for (2S)-2 and (2R)-2 respectively, about a 3-fold difference between enantiomers. Data are presented showing direct antagonism of acetylcholine in the guinea pig ileum assay. In a comparison of the anticholinergic effects of 2 and 1, the metabolite (2) was slightly less potent than disopyramide (1).

  DOI：

  10.1021/jm00137a024

文献信息

• LE, CORRE PASCAL;GIBASSIER, DENIS;SADO, PIERRE;LE, VERGE ROGER, J. CHROMATOGR., 450,(1988) N 2, C. 211-216
  作者：LE, CORRE PASCAL、GIBASSIER, DENIS、SADO, PIERRE、LE, VERGE ROGER

  DOI：——

  日期：——
• Synthesis and anticholinergic properties of the enantiomers of 4-(isopropylamino)-2-(2-pyridyl)-2-phenylbutyramide, the mono-N-dealkylated metabolite of disopyramide
  作者：Wendel L. Nelson、Cherilyn K. Sneed、Kathleen M. Giacomini、John C. Giacomini、John Stauss、Terrence F. Blaschke、Brian M. Cox

  DOI：10.1021/jm00137a024

  日期：1981.5

  The 2R and 2S enantiomers of 4-isopropyl-2-(2-pyridyl)-2-phenylbutyramide [(2R)-2 and (2S)-2] were prepared from the respective 2R and 2S enantiomers of disopyramide [(2R)-1 and (2S)-1] by oxidation with peracid, Cope elimination, and subsequent zinc/HCl reduction of the resulting hydroxylamines (2R)-3 and (2S)-3. The enantiomers were tested as antagonists to the contraction of guinea pig ileum longitudinal muscle produced in response to electrically stimulated release of acetylcholine. The enantiomers showed IC50 values of 5.0 X 10(-6) and 14 X 10(-6) M for (2S)-2 and (2R)-2 respectively, about a 3-fold difference between enantiomers. Data are presented showing direct antagonism of acetylcholine in the guinea pig ileum assay. In a comparison of the anticholinergic effects of 2 and 1, the metabolite (2) was slightly less potent than disopyramide (1).