4-[[4-[[1-(3-aminopropyl)-4-formamidoimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-N-[2-(dimethylamino)ethyl]-1-methylimidazole-2-carboxamide | 1400503-27-6

• 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: 4-[[4-[[1-(3-aminopropyl)-4-formamidoimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-N-[2-(dimethylamino)ethyl]-1-methylimidazole-2-carboxamide
• CAS: 1400503-27-6
• 化学式: C₂₃H₃₃N₁₁O₄
• 分子量: 527.586
• InChiKey: DNMWMFWKECFDTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(3-chloropropyl)-4-nitroimidazole-2-carboxylic acid 在 草酰氯 、 5%-palladium/activated carbon 、 氨 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 70.75h， 生成 4-[[4-[[1-(3-aminopropyl)-4-formamidoimidazole-2-carbonyl]amino]-1-methylpyrrole-2-carbonyl]amino]-N-[2-(dimethylamino)ethyl]-1-methylimidazole-2-carboxamide
  参考文献：
  名称：

  Synthesis and DNA binding properties of 1-(3-aminopropyl)-imidazole-containing triamide f-Im∗PyIm: A novel diamino polyamide designed to target 5′-ACGCGT-3′

  摘要：

  A novel diamino/dicationic polyamide f-Im*PyIm (5) that contains an orthogonally positioned aminopropyl chain on an imidazole (Im*) moiety was designed to target 5'-ACGCGT-3'. The DNA binding properties of the diamino polyamide 5, determined by CD, Delta T-M, DNase I footprinting, SPR, and ITC studies, were compared with those of its monoamino/monocationic counterpart f-ImPyIm (1) and its diamino/dicationic isomer f-ImPy*Im (2), which has the aminopropyl group attached to the central pyrrole unit (Py*). The results gave evidence for the minor groove binding and selectivity of polyamide 5 for the cognate sequence 5'-ACGCGT-3', and with strong affinity (K-eq = 2.3 x 10(7) M-1). However, the binding affinities varied according to the order: f-ImPy*Im (2) > f-ImPyIm (1) >= f-Im*PyIm (5) confirming that the second amino group can improve affinity, but its position within the polyamide can affect affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.071