N-(5-aminopyrimidin-4-yl)-1-methyl-4-nitropyrrole-2-carboxamide | 682748-60-3

• 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: N-(5-aminopyrimidin-4-yl)-1-methyl-4-nitropyrrole-2-carboxamide
• CAS: 682748-60-3
• 化学式: C₁₀H₁₀N₆O₃
• 分子量: 262.228
• InChiKey: YQHIFIUIIZCHLF-UHFFFAOYSA-N

物化性质

• 沸点：
  419.3±45.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(5-aminopyrimidin-4-yl)-1-methyl-4-nitropyrrole-2-carboxamide 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 4-[(3-chlorothiophene-2-carbonyl)amino]-1-[3-(dimethylamino)propyl]-N-[1-methyl-5-(7H-purin-8-yl)pyrrol-3-yl]pyrrole-2-carboxamide
  参考文献：
  名称：

  DNA binding ligands targeting drug-resistant Gram-positive bacteria. Part 2: C-terminal benzimidazoles and derivatives

  摘要：

  The synthesis and in vitro potency of DNA minor-groove binding antibacterials lacking the C-terminal amide bond are described. The crescent shaped molecules bear the positively charged amino group at an internal pyrrole unit instead of the C-terminus. Three structural parameters were investigated: the N-terminal unit, the internal amino group, and the C-terminal ring system. Several compounds demonstrated good in vitro potency against various Gram-positive bacteria and some molecules were moderately active against Escherichia coli, a representative Gram-negative strain. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.043
• 作为产物：
  描述：

  4,5-二氨基嘧啶 、 1-甲基-4-硝基吡咯-2-羧酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以35%的产率得到N-(5-aminopyrimidin-4-yl)-1-methyl-4-nitropyrrole-2-carboxamide
  参考文献：
  名称：

  DNA binding ligands targeting drug-resistant Gram-positive bacteria. Part 2: C-terminal benzimidazoles and derivatives

  摘要：

  The synthesis and in vitro potency of DNA minor-groove binding antibacterials lacking the C-terminal amide bond are described. The crescent shaped molecules bear the positively charged amino group at an internal pyrrole unit instead of the C-terminus. Three structural parameters were investigated: the N-terminal unit, the internal amino group, and the C-terminal ring system. Several compounds demonstrated good in vitro potency against various Gram-positive bacteria and some molecules were moderately active against Escherichia coli, a representative Gram-negative strain. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.043

文献信息

• ANTI-INFECTIVE BIARYL COMPOUNDS
  申请人：Jones Peter

  公开号：US20080090816A1

  公开（公告）日：2008-04-17

  Compounds represented by the formula where R 1 , R 2 , R 3 , R 4 , R 5 , and Q are as defined herein, exhibit activity against infectious pathogens.
• US7265129B2
  申请人：——

  公开号：US7265129B2

  公开（公告）日：2007-09-04
• DNA binding ligands targeting drug-resistant Gram-positive bacteria. Part 2: C-terminal benzimidazoles and derivatives
  作者：Roland W. Bürli、Peter Jones、Dustin McMinn、Quan Le、Jian-Xin Duan、Jacob A. Kaizerman、Stacey Difuntorum、Heinz E. Moser

  DOI：10.1016/j.bmcl.2003.12.043

  日期：2004.3

  The synthesis and in vitro potency of DNA minor-groove binding antibacterials lacking the C-terminal amide bond are described. The crescent shaped molecules bear the positively charged amino group at an internal pyrrole unit instead of the C-terminus. Three structural parameters were investigated: the N-terminal unit, the internal amino group, and the C-terminal ring system. Several compounds demonstrated good in vitro potency against various Gram-positive bacteria and some molecules were moderately active against Escherichia coli, a representative Gram-negative strain. (C) 2003 Elsevier Ltd. All rights reserved.