(2α,5α,7α,8aβ)-4-amino-5-chloro-2-methoxy-N-(octahydro-5-methyl-2-phenylindolizin-7-yl)benzamide | 115114-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2α,5α,7α,8aβ)-4-amino-5-chloro-2-methoxy-N-(octahydro-5-methyl-2-phenylindolizin-7-yl)benzamide
• CAS: 115114-04-0
• 化学式: C₂₃H₂₈ClN₃O₂
• 分子量: 413.947
• InChiKey: PKZKDNACFVSZIJ-UBDQQSCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.59
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  α-(2,2-diethoxyethyl)benzyl cyanide 在 吡啶 、 aluminium hydride 、 盐酸 、 sodium hydroxide 、 戊醇 、 盐酸羟胺 、 sodium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2α,5α,7α,8aβ)-4-amino-5-chloro-2-methoxy-N-(octahydro-5-methyl-2-phenylindolizin-7-yl)benzamide
  参考文献：
  名称：

  Substituted benzamides with conformationally restricted side chains. 2. Indolizidine derivatives as central dopamine receptor antagonists

  摘要：

  The substituted benzamides metoclopramide (1) and clebopride (3) are stimulants of gastric motility. They are also central dopamine receptor antagonists with 3 being the more potent. This is presumed to be due to an additional interaction of its N-benzyl group with the receptor. The effect of restricting the conformation of this group by replacing the N-benzylpiperidine side chain of 3 by phenyl-substituted quinolizidines and indolizidines has been investigated. Only the indolizidines had significant activity, the nature of which depended upon the orientation of the phenyl substituent. The 2 alpha-phenyl isomers 5d-h were potent central dopamine D2 receptor antagonists with 5h showing selectivity for the limbic system. The 2 beta-phenyl isomer 5c was a gastric motility stimulant devoid of significant central dopamine receptor antagonist activity. Implications on receptor models are discussed.

  DOI：

  10.1021/jm00117a008