7-methoxy-1-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indole-4-ol | 1431634-01-3

• 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: 7-methoxy-1-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indole-4-ol
• 英文别名: 7-Methoxy-1-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)indol-4-ol
• CAS: 1431634-01-3
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: XOAGVKBERXDBJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.31
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-methoxy-1-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indole-4-ol 、 N-α-(叔丁氧基羰基)-L-色氨醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 生成 tert-butyl (S)-(1-(1H-indol-3-yl)-3-((7-methoxy-1-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indol-4-yl)oxy)propan-2-yl)carbamate
  参考文献：
  名称：

  Design, synthesis and evaluation of novel indole derivatives as AKT inhibitors

  摘要：

  Herein, we describe the discovery and synthesis of a new series of 1,2,4,7-tetra-substituted indole derivatives as novel AKT inhibitors by optimization of a weak hit methyl 4-(2-aminoethoxy)-1H-indole-2-carboxylate (1). Both representative compounds 6a and 6o exhibited the most potent inhibitory activities against AKT1, with inhibition rates of 72.5% and 78.6%, respectively, at concentrations of 10 nM. In addition, compounds 6a and 6o also potently inhibited the phosphorylation of the downstream GSK3 protein and displayed slightly better anti-proliferative activities in a prostate cancer cell line. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.022
• 作为产物：
  描述：

  5-(7-Methoxy-1-methyl-4-phenylmethoxyindol-2-yl)-3-methyl-1,2,4-oxadiazole 在 aluminum (III) chloride 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以89%的产率得到7-methoxy-1-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indole-4-ol
  参考文献：
  名称：

  Design, synthesis and evaluation of novel indole derivatives as AKT inhibitors

  摘要：

  Herein, we describe the discovery and synthesis of a new series of 1,2,4,7-tetra-substituted indole derivatives as novel AKT inhibitors by optimization of a weak hit methyl 4-(2-aminoethoxy)-1H-indole-2-carboxylate (1). Both representative compounds 6a and 6o exhibited the most potent inhibitory activities against AKT1, with inhibition rates of 72.5% and 78.6%, respectively, at concentrations of 10 nM. In addition, compounds 6a and 6o also potently inhibited the phosphorylation of the downstream GSK3 protein and displayed slightly better anti-proliferative activities in a prostate cancer cell line. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.022