2-(4-{[4-(tert-butoxycarbonylmethyl-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-imidazol-2-yl)-4-methoxy-1H-benzoimidazole-5-carboxylic acid methyl ester | 918304-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-{[4-(tert-butoxycarbonylmethyl-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-imidazol-2-yl)-4-methoxy-1H-benzoimidazole-5-carboxylic acid methyl ester
• CAS: 918304-06-0
• 化学式: C₂₅H₂₉N₇O₆
• 分子量: 523.549
• InChiKey: ZVJTWHWWSNZWHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  154.39
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(4-{[4-(tert-butoxycarbonylmethyl-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-imidazol-2-yl)-4-methoxy-1H-benzoimidazole-5-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以98%的产率得到2-(4-{[4-(tert-butoxycarbonylmethyl-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-imidazol-2-yl)-4-methoxy-1H-benzoimidazole-5-carboxylic acid
  参考文献：
  名称：

  Exploring the limits of benzimidazole DNA-binding oligomers for the hypoxia inducible factor (HIF) site

  摘要：

  The vascular endothelial growth factor (VEGF) and its receptors have been implicated as key-factors in tumor angiogenesis and are major targets in cancer therapy. New oligomers which mimic the architecture of DNA-binding polyamides have been designed to target the hypoxia inducible factor (HIF-1 alpha) binding site on the promoter of VEGF gene. These oligomers incorporate an increasing number of six-five fused rings such as hydroxybenzimidazole-imidazole, benzimidazole pyrrole, benzimidazole-chlorothiophene, and imidazopyridine-pyrrole, and bind the VEGF hypoxia response element (HRE) 5'-TACGT-3' with high affinity and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.028
• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、506.66 kPa 条件下， 反应 65.0h， 生成 2-(4-{[4-(tert-butoxycarbonylmethyl-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-imidazol-2-yl)-4-methoxy-1H-benzoimidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Exploring the limits of benzimidazole DNA-binding oligomers for the hypoxia inducible factor (HIF) site

  摘要：

  The vascular endothelial growth factor (VEGF) and its receptors have been implicated as key-factors in tumor angiogenesis and are major targets in cancer therapy. New oligomers which mimic the architecture of DNA-binding polyamides have been designed to target the hypoxia inducible factor (HIF-1 alpha) binding site on the promoter of VEGF gene. These oligomers incorporate an increasing number of six-five fused rings such as hydroxybenzimidazole-imidazole, benzimidazole pyrrole, benzimidazole-chlorothiophene, and imidazopyridine-pyrrole, and bind the VEGF hypoxia response element (HRE) 5'-TACGT-3' with high affinity and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.028