ethyl (1R,2R)-1-{[(S)-N-(tert-butoxycarbonyl)alanyl]oxy}-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate | 908338-35-2

• 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: ethyl (1R,2R)-1-{[(S)-N-(tert-butoxycarbonyl)alanyl]oxy}-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate
• CAS: 908338-35-2
• 化学式: C₂₂H₂₈N₂O₆
• 分子量: 416.474
• InChiKey: ADWLADKDGBCTHE-JCKWVBRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.86
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl (1R,2R)-1-{[(S)-N-(tert-butoxycarbonyl)alanyl]oxy}-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、273.58 kPa 条件下， 反应 6.0h， 以80%的产率得到(S)-2,3-Dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCβ-selective inhibitors

  摘要：

  Conformationally restricted 3-anilino-4-(3-indolyl)maleimide derivatives were designed and synthesized aiming at discovery of novel protein kinase C beta (PKC beta)-selective inhibitors possessing oral bioavailability. Among them, compounds having a fused five-membered ring at the indole 1,2-position inhibited PKC beta 2 with IC50 of nM-order and showed good oral bioavailability. One of the most potent compounds was found to be PKC beta-selective over other 6 isozymes and exhibited ameliorative effects in a rat diabetic retinopathy model via oral route. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.033
• 作为产物：
  描述：

  ethyl 2,3-dihydro-1-oxo-1H-pyrrolo[1,2-a]indole-2-carboxylate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 ethyl (1R,2R)-1-{[(S)-N-(tert-butoxycarbonyl)alanyl]oxy}-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate
  参考文献：
  名称：

  Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCβ-selective inhibitors

  摘要：

  Conformationally restricted 3-anilino-4-(3-indolyl)maleimide derivatives were designed and synthesized aiming at discovery of novel protein kinase C beta (PKC beta)-selective inhibitors possessing oral bioavailability. Among them, compounds having a fused five-membered ring at the indole 1,2-position inhibited PKC beta 2 with IC50 of nM-order and showed good oral bioavailability. One of the most potent compounds was found to be PKC beta-selective over other 6 isozymes and exhibited ameliorative effects in a rat diabetic retinopathy model via oral route. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.033