Acetic acid (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1H-indol-2-ylmethyl)-propyl ester | 257876-19-0

• 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: Acetic acid (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1H-indol-2-ylmethyl)-propyl ester
• CAS: 257876-19-0
• 化学式: C₃₀H₃₅NO₃Si
• 分子量: 485.698
• InChiKey: ABADOVPCTRIDOX-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1H-indol-2-ylmethyl)-propyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 (S)-2-(tert-butyldiphenylsilyloxymethyl)-3-(1H-indol-2-yl)propan-1-ol
  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：

  diethyl (1H-indol-2-ylmethylene)malonate 在 Lipase PS 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Acetic acid (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(1H-indol-2-ylmethyl)-propyl 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