3-[(S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl]-4-phenylamino-pyrrole-2,5-dione | 908338-25-0

• 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: 3-[(S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl]-4-phenylamino-pyrrole-2,5-dione
• CAS: 908338-25-0
• 化学式: C₃₉H₃₉N₃O₃Si
• 分子量: 625.842
• InChiKey: ADDKXGCGRVKPPA-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.36
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-[(S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl]-4-phenylamino-pyrrole-2,5-dione 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-anilino-4-[(S)-8-(methanesulfonyloxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-1H-pyrrole-2,5-dione
  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：

  2-[(S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl]-2-hydroxy-acetamide 在 三乙基硅烷 、 potassium tert-butylate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-[(S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl]-4-phenylamino-pyrrole-2,5-dione
  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