7-[5-(7-Acetylamino-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-5-oxo-pentanoylamino]-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester | 261763-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-[5-(7-Acetylamino-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-5-oxo-pentanoylamino]-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester
• CAS: 261763-69-3
• 化学式: C₅₂H₅₂Cl₂N₄O₇
• 分子量: 915.913
• InChiKey: STAAKBMMGKRFLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.66
• 重原子数：
  65.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  126.51
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-[5-(7-Acetylamino-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-5-oxo-pentanoylamino]-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 甲酸铵 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到7-[5-(7-Acetylamino-1-chloromethyl-5-hydroxy-1,2-dihydro-benzo[e]indol-3-yl)-5-oxo-pentanoylamino]-1-chloromethyl-5-hydroxy-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and cytotoxicity evaluation of 1-chloromethyl-5-hydroxy-1,2-dihydro-3 H -benz[ e ]indole ( seco -CBI) dimers

  摘要：

  Three types of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) dimers were designed, synthesized and evaluated in vitro by NCI against nine types of cancer cells. Biological results showed that the antitumor activities of these seco-CBI dimers were strongly related to the position and length of the linker and generally with potency increasing in the order of C7-C7 dimers (22i-iv) < C7-N3 dimers (28i-iv) < N3-N3 dimers (25i-iv). Compound 28iv showed significant activity against CCRT-CEM, HL-60 (TB), MOLT-4, and SR leukemia cell lines and the MCF 7 breast cancer cell line with GI(50) values < 0.01 mu M. N3-N3 dimer 25i displayed striking potency against leukemia, CNS cancer, melanoma and prostate cancer cell lines with GI(50) values < 0.01 mu M against all the cell lines and showed the highest overall potency of the agents examined (GMG = 0.0120 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00088-2
• 作为产物：
  描述：

  5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-chloromethyl-7-(9-fluorenylmethyloxy-carbonylamino)-1,2-dihydro-3H-benz[e]indole 在 盐酸 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 7-[5-(7-Acetylamino-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-5-oxo-pentanoylamino]-5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and cytotoxicity evaluation of 1-chloromethyl-5-hydroxy-1,2-dihydro-3 H -benz[ e ]indole ( seco -CBI) dimers

  摘要：

  Three types of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) dimers were designed, synthesized and evaluated in vitro by NCI against nine types of cancer cells. Biological results showed that the antitumor activities of these seco-CBI dimers were strongly related to the position and length of the linker and generally with potency increasing in the order of C7-C7 dimers (22i-iv) < C7-N3 dimers (28i-iv) < N3-N3 dimers (25i-iv). Compound 28iv showed significant activity against CCRT-CEM, HL-60 (TB), MOLT-4, and SR leukemia cell lines and the MCF 7 breast cancer cell line with GI(50) values < 0.01 mu M. N3-N3 dimer 25i displayed striking potency against leukemia, CNS cancer, melanoma and prostate cancer cell lines with GI(50) values < 0.01 mu M against all the cell lines and showed the highest overall potency of the agents examined (GMG = 0.0120 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00088-2