2-{1-[(R)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide | 257876-71-4

• 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-{1-[(R)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide
• CAS: 257876-71-4
• 化学式: C₃₅H₄₆N₂O₄Si
• 分子量: 586.847
• InChiKey: ULDOTOPBEBEHPE-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-{1-[(R)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide 在 palladium on activated charcoal 三氟乙酸 、 氢气 作用下， 以 氯仿 、 水 、 乙醇 为溶剂， 反应 3.5h， 以95%的产率得到2-[(R)-7-(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
• 作为产物：
  描述：

  (R)-2-(2,2-二乙氧基乙基)-1,3-丙二醇单醋酸盐 在 咪唑 、 sodium hydroxide 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.42h， 生成 2-{1-[(R)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-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