2-[(S)-8-(tert-butyldiphenylsilyloxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetamide | 257874-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[(S)-8-(tert-butyldiphenylsilyloxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetamide
• CAS: 257874-97-8
• 化学式: C₃₁H₃₆N₂O₂Si
• 分子量: 496.725
• InChiKey: SYNCZGUZCXAKFR-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.25
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[(S)-8-(tert-butyldiphenylsilyloxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetamide 在 potassium tert-butylate 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-((S)-8-Hydroxymethyl-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
• 作为产物：
  描述：

  (S)-8-(hydroxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indole 在 咪唑 、 三乙基硅烷 、 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2-[(S)-8-(tert-butyldiphenylsilyloxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetamide
  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