methyl 1-isopropyl-2-methyl-1H-indole-3-carboxylate | 1802175-10-5

• 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 1-isopropyl-2-methyl-1H-indole-3-carboxylate
• 英文别名: 1H-Indole-3-carboxylic acid, 2-methyl-1-(1-methylethyl)-, methyl ester；methyl 2-methyl-1-propan-2-ylindole-3-carboxylate
• CAS: 1802175-10-5
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: KNAINFXXBCNAGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 1-isopropyl-2-methyl-1H-indole-3-carboxylate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以94%的产率得到1-isopropyl-2-methyl-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Discovery, design, and synthesis of indole-based EZH2 inhibitors

  摘要：

  The discovery and optimization of a series of small molecule EZH2 inhibitors is described. Starting from dimethylpyridone HTS hit (2), a series of indole-based EZH2 inhibitors were identified. Biochemical potency and microsomal stability were optimized during these studies and afforded compound 22. This compound demonstrates nanomolar levels of biochemical potency (IC50 = 0.002 mu M), cellular potency (EC50 = 0.080 mu M), and afforded tumor regression when dosed (200 mpk SC BID) in an EZH2 dependent tumor xenograft model. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.056
• 作为产物：
  描述：

  2-甲基-1H-吲哚-3-甲酸甲酯 、 2-溴丙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以36%的产率得到methyl 1-isopropyl-2-methyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Discovery, design, and synthesis of indole-based EZH2 inhibitors

  摘要：

  The discovery and optimization of a series of small molecule EZH2 inhibitors is described. Starting from dimethylpyridone HTS hit (2), a series of indole-based EZH2 inhibitors were identified. Biochemical potency and microsomal stability were optimized during these studies and afforded compound 22. This compound demonstrates nanomolar levels of biochemical potency (IC50 = 0.002 mu M), cellular potency (EC50 = 0.080 mu M), and afforded tumor regression when dosed (200 mpk SC BID) in an EZH2 dependent tumor xenograft model. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.056