[3-[5-[[4-[[4-[[4-[[4-[4-[[4-[[4-[[4-[3-[[4-[(4-acetamido-1-methylpyrrole-2-carbonyl)amino]-1-methylimidazole-2-carbonyl]amino]propanoylamino]-1-methylimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]butanoylamino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1H-indole-2-carbonyl]-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-5-yl] (2S)-2,6-diaminohexanoate | 1345823-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: [3-[5-[[4-[[4-[[4-[[4-[4-[[4-[[4-[[4-[3-[[4-[(4-acetamido-1-methylpyrrole-2-carbonyl)amino]-1-methylimidazole-2-carbonyl]amino]propanoylamino]-1-methylimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]butanoylamino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1H-indole-2-carbonyl]-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-5-yl] (2S)-2,6-diaminohexanoate
• CAS: 1345823-55-3
• 化学式: C₈₉H₉₆ClN₂₇O₁₅
• 分子量: 1819.37
• InChiKey: QKKWOWWHBKJXFE-ZXZJTQSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  132
• 可旋转键数：
  35
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  534
• 氢给体数：
  15
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [3-[5-[[4-[[4-[[4-[[4-[4-[[4-[[4-[[4-[3-[[4-[(4-acetamido-1-methylpyrrole-2-carbonyl)amino]-1-methylimidazole-2-carbonyl]amino]propanoylamino]-1-methylimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]butanoylamino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1H-indole-2-carbonyl]-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-5-yl] (2S)-2,6-diaminohexanoate 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[3-[[4-[(4-acetamido-1-methylpyrrole-2-carbonyl)amino]-1-methylimidazole-2-carbonyl]amino]propanoylamino]-N-[5-[[5-[[4-[[5-[[5-[[5-[[5-[[2-[1-(chloromethyl)-5-hydroxy-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]amino]-4-oxobutyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylimidazole-2-carboxamide
  参考文献：
  名称：

  Evaluation of PI polyamide conjugates with eight-base pair recognition and improvement of the aqueous solubility by PEGylation

  摘要：

  To investigate the effect of elongating base-pair (bp) recognition sequences, we synthesized N-methylpyrrole-N-methylimidazole (PI) polyamide conjugates with eight-bp recognition (3-5). The DNA alkylating activities of conjugates 3-5 were evaluated by high-resolution denaturing polyacrylamide gel electrophoresis with a 208-bp DNA fragment. Conjugates 3-5 showed high alkylating activities at nanomolar concentrations.We then addressed the following issue about PI conjugates. Generally, PI polyamide conjugates hardly dissolve in aqueous solution. To improve the aqueous solubility, by the introduction of hydrophilic groups, we synthesized PI polyamide conjugates that were modified with a seco-CBI moiety (6-11). Conjugates 9-11 that were modified by methoxypolyethylene glycol (PEG) 750 acquired moderate solubility and stability in aqueous solution. In addition, conjugates 10 and 11 had high cytotoxicity against A549 and DU145. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.009
• 作为产物：
  描述：

  在 盐酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 以1.5 mg的产率得到[3-[5-[[4-[[4-[[4-[[4-[4-[[4-[[4-[[4-[3-[[4-[(4-acetamido-1-methylpyrrole-2-carbonyl)amino]-1-methylimidazole-2-carbonyl]amino]propanoylamino]-1-methylimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]butanoylamino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1H-indole-2-carbonyl]-1-(chloromethyl)-1,2-dihydrobenzo[e]indol-5-yl] (2S)-2,6-diaminohexanoate
  参考文献：
  名称：

  Evaluation of PI polyamide conjugates with eight-base pair recognition and improvement of the aqueous solubility by PEGylation

  摘要：

  To investigate the effect of elongating base-pair (bp) recognition sequences, we synthesized N-methylpyrrole-N-methylimidazole (PI) polyamide conjugates with eight-bp recognition (3-5). The DNA alkylating activities of conjugates 3-5 were evaluated by high-resolution denaturing polyacrylamide gel electrophoresis with a 208-bp DNA fragment. Conjugates 3-5 showed high alkylating activities at nanomolar concentrations.We then addressed the following issue about PI conjugates. Generally, PI polyamide conjugates hardly dissolve in aqueous solution. To improve the aqueous solubility, by the introduction of hydrophilic groups, we synthesized PI polyamide conjugates that were modified with a seco-CBI moiety (6-11). Conjugates 9-11 that were modified by methoxypolyethylene glycol (PEG) 750 acquired moderate solubility and stability in aqueous solution. In addition, conjugates 10 and 11 had high cytotoxicity against A549 and DU145. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.009