4-amino-N-[5-[[5-[[(3E)-3-amino-3-hydroxyiminopropyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide | 288153-11-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-amino-N-[5-[[5-[[(3E)-3-amino-3-hydroxyiminopropyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide
• CAS: 288153-11-7
• 化学式: C₂₁H₂₇N₉O₄
• 分子量: 469.503
• InChiKey: DLGNWGWFCVPGIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  187
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(2-bromoacryloyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid chloride 、 4-amino-N-[5-[[5-[[(3E)-3-amino-3-hydroxyiminopropyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide 生成 N-(3-amino-3-hydroxyiminopropyl)-4-[[4-[[4-[[4-(2-bromoprop-2-enoylamino)-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-1-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety

  摘要：

  The design, synthesis, in vitro and in vivo activities of novel alpha-bromoacrylic derivatives of distamycin A, modified at the amidino moiety by the replacement with basic or non-basic groups are reported. In spite of the relevance of these modifications of distamycin frame, the new derivatives are potent cytotoxics. The presence of the amidino moiety, is, therefore, not an absolute requirement for the activity. In particular due to a favorable myclotoxicity/cytotoxicity ratio, guanidino derivative PNU 166196 was selected for clinical development. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00205-5
• 作为产物：
  描述：

  3-[1-Methyl-4[1-methyl-4[1-methyl-4-formamidopyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidoxime 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 4-amino-N-[5-[[5-[[(3E)-3-amino-3-hydroxyiminopropyl]carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety

  摘要：

  The design, synthesis, in vitro and in vivo activities of novel alpha-bromoacrylic derivatives of distamycin A, modified at the amidino moiety by the replacement with basic or non-basic groups are reported. In spite of the relevance of these modifications of distamycin frame, the new derivatives are potent cytotoxics. The presence of the amidino moiety, is, therefore, not an absolute requirement for the activity. In particular due to a favorable myclotoxicity/cytotoxicity ratio, guanidino derivative PNU 166196 was selected for clinical development. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00205-5