1H-Benz[e]indol-5-ol,3-(1H-benz[f]indol-2-ylcarbonyl)-1-(chloromethyl)-2,3-dihydro-, (1R)- | 647022-69-3

• 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: 1H-Benz[e]indol-5-ol,3-(1H-benz[f]indol-2-ylcarbonyl)-1-(chloromethyl)-2,3-dihydro-, (1R)-
• 英文别名: 3-[benz[f]indole-2-carbonyl]-1-(R)-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benz[e]indole
• CAS: 647022-69-3
• 化学式: C₂₆H₁₉ClN₂O₂
• 分子量: 426.902
• InChiKey: ASECPNWMBNEECC-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1H-Benz[e]indol-5-ol,3-(1H-benz[f]indol-2-ylcarbonyl)-1-(chloromethyl)-2,3-dihydro-, (1R)- 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以58%的产率得到N²-[(benz[f]indole-2-yl)carbonyl]-(8bS,9aR)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
  参考文献：
  名称：

  Establishment of substituent effects in the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065

  摘要：

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be greater than or equal to 1000- fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC50 = 2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00194-9
• 作为产物：
  描述：

  (R)-1-(氯甲基)-5-羟基-1,2-二氢-3H-苯并[E]吲哚-3-羧酸叔丁酯 在 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1H-Benz[e]indol-5-ol,3-(1H-benz[f]indol-2-ylcarbonyl)-1-(chloromethyl)-2,3-dihydro-, (1R)-
  参考文献：
  名称：

  Establishment of substituent effects in the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065

  摘要：

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be greater than or equal to 1000- fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC50 = 2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00194-9

文献信息

• Establishment of substituent effects in the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065
  作者：Jay P. Parrish、David B. Kastrinsky、Frederic Stauffer、Michael P. Hedrick、Inkyu Hwang、Dale L. Boger

  DOI：10.1016/s0968-0896(03)00194-9

  日期：2003.8

  An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be greater than or equal to 1000- fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC50 = 2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. (C) 2003 Elsevier Ltd. All rights reserved.