(R)-5-chloro-3-(5-((dimethylamino)methyl)-2-methoxyphenyl)-1-(4-methoxyphenylsulfonyl)-3-((S)-2-(oxazol-2-yl)pyrrolidin-1-yl)indolin-2-one | 1313729-30-4

• 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: (R)-5-chloro-3-(5-((dimethylamino)methyl)-2-methoxyphenyl)-1-(4-methoxyphenylsulfonyl)-3-((S)-2-(oxazol-2-yl)pyrrolidin-1-yl)indolin-2-one
• 英文别名: (3R)-5-chloro-3-[5-[(dimethylamino)methyl]-2-methoxyphenyl]-1-(4-methoxyphenyl)sulfonyl-3-[(2S)-2-(1,3-oxazol-2-yl)pyrrolidin-1-yl]indol-2-one
• CAS: 1313729-30-4
• 化学式: C₃₂H₃₃ClN₄O₆S
• 分子量: 637.156
• InChiKey: OAIPTJXKMLWSCX-GMCHKSTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-Chloro-3-[5-(5,5-dimethyl-[1,3]dioxan-2-yl)-2-methoxyphenyl]-3-((S)-2-oxazol-2-yl-pyrrolidin-1-yl)-1,3-dihydroindol-2-one 在 盐酸 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (R)-5-chloro-3-(5-((dimethylamino)methyl)-2-methoxyphenyl)-1-(4-methoxyphenylsulfonyl)-3-((S)-2-(oxazol-2-yl)pyrrolidin-1-yl)indolin-2-one
  参考文献：
  名称：

  Potent and selective oxindole-based vasopressin 1b receptor antagonists with improved pharmacokinetic properties

  摘要：

  Herein we report the discovery of a novel series of vasopressin 1b (V1b) receptor antagonists, starting from potent but metabolically labile oxindole SSR149415. Masking the proline N,N-dimethyl amide moiety as an oxazole and attaching a benzylic amine moiety to the northern phenyl ring resulted in potent and selective V1b receptor antagonists with improved metabolic stability and improved pharmacokinetic properties in rat. Compound 18c was found to be efficacious in a rat model of anti-depressant activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.012

文献信息

• Potent and selective oxindole-based vasopressin 1b receptor antagonists with improved pharmacokinetic properties
  作者：Thorsten Oost、Gisela Backfisch、Swati Bhowmik、Marcel M. van Gaalen、Hervé Geneste、Wilfried Hornberger、Wilfried Lubisch、Astrid Netz、Liliane Unger、Wolfgang Wernet

  DOI：10.1016/j.bmcl.2011.03.012

  日期：2011.6

  Herein we report the discovery of a novel series of vasopressin 1b (V1b) receptor antagonists, starting from potent but metabolically labile oxindole SSR149415. Masking the proline N,N-dimethyl amide moiety as an oxazole and attaching a benzylic amine moiety to the northern phenyl ring resulted in potent and selective V1b receptor antagonists with improved metabolic stability and improved pharmacokinetic properties in rat. Compound 18c was found to be efficacious in a rat model of anti-depressant activity. (C) 2011 Elsevier Ltd. All rights reserved.