methyl 7-bromo-4-hydroxy-1-methyl-1H-indole-2-carboxylate | 1431634-11-5

• 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: methyl 7-bromo-4-hydroxy-1-methyl-1H-indole-2-carboxylate
• 英文别名: methyl 7-bromo-4-hydroxy-1-methylindole-2-carboxylate
• CAS: 1431634-11-5
• 化学式: C₁₁H₁₀BrNO₃
• 分子量: 284.109
• InChiKey: JSZPKCSFNRPXFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 7-bromo-4-hydroxy-1-methyl-1H-indole-2-carboxylate 、 N-Boc-D-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 methyl (R)-7-bromo-4-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propoxy)-1-methyl-1H-indole-2-carboxylate
  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：

  methyl 4-(benzyloxy)-7-bromo-1-methyl-1H-indole-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以69%的产率得到methyl 7-bromo-4-hydroxy-1-methyl-1H-indole-2-carboxylate
  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

文献信息

• Design, synthesis, and evaluation of novel Akt1 inhibitors based on an indole scaffold
  作者：Dezhi Yang、Dongdong Tong、Qian Zhang、Yongtao Wang、Jing Sun、Fenghe Zhang、Guisen Zhao

  DOI：10.1111/cbdd.13000

  日期：2017.11

  A novel series of indole derivatives targeting the Akt1 were designed and synthesized. Compound 19b exhibited the most potent inhibitory activity against Akt1 with inhibition rate of 70.3% at the concentration of 10 nm and fivefold higher antiproliferative activity against PC-3 cell with IC50 value of 3.1 ± 0.1 μm than positive control (15.5 ± 0.4 μm).

  设计并合成了一系列针对Akt1的新型吲哚衍生物。化合物19B具有70.3％的抑制率表现出最有效的抑制活性对Akt1的在10浓度n米和五倍更高的抗增殖活性针对PC-3细胞与IC 50为3.1±0.1μ值米比阳性对照（15.5±0.4 μ米）。