5-benzoylamino-4-bromoindole-1-carboxylic acid tert-butyl ester | 1448607-77-9

• 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: 5-benzoylamino-4-bromoindole-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 5-benzamido-4-bromoindole-1-carboxylate；tert-butyl 5-benzamido-4-bromoindole-1-carboxylate
• CAS: 1448607-77-9
• 化学式: C₂₀H₁₉BrN₂O₃
• 分子量: 415.286
• InChiKey: HPSSCJKAMIZGLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzoylamino-4-bromoindole-1-carboxylic acid tert-butyl ester 在 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 sodium hydride 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 32.75h， 生成 (1-(chloromethyl)-1,2-dihydropyrrolo[3,2-e]indol-3(6H)-yl)(5-fluoro-1H-indol-2-yl)methanone
  参考文献：
  名称：

  Re-engineering of the Duocarmycin Structural Architecture Enables Bioprecursor Development Targeting CYP1A1 and CYP2W1 for Biological Activity

  摘要：

  A library of duocarmycin bioprecursors based on the CPI and CBI scaffolds was synthesized and used to probe selective activation by cells expressing CYP1A1 and 2W1, CYPs known to be expressed in high frequency in some tumors. Several CPI-based compounds were pM-nM potent in CYP1A1 expressing cells. CYP2W1 was also shown to sensitize proliferating cells to several compounds, demonstrating its potential as a target for tumor selective activation of duocarmycin bioprecursors.

  DOI：

  10.1021/jm4000209
• 作为产物：
  描述：

  N-Boc-5-氨基吲哚 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 5-benzoylamino-4-bromoindole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Re-engineering of the Duocarmycin Structural Architecture Enables Bioprecursor Development Targeting CYP1A1 and CYP2W1 for Biological Activity

  摘要：

  A library of duocarmycin bioprecursors based on the CPI and CBI scaffolds was synthesized and used to probe selective activation by cells expressing CYP1A1 and 2W1, CYPs known to be expressed in high frequency in some tumors. Several CPI-based compounds were pM-nM potent in CYP1A1 expressing cells. CYP2W1 was also shown to sensitize proliferating cells to several compounds, demonstrating its potential as a target for tumor selective activation of duocarmycin bioprecursors.

  DOI：

  10.1021/jm4000209