1-(2-hydroxyethyl)-4-{2-[1-methyl-4-(4-(4-amino-1-methyl-2-pyrrolecarboxamido)-1-benzamido)-2-imidazolecarboxamido]ethyl}piperidine | 758727-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-hydroxyethyl)-4-{2-[1-methyl-4-(4-(4-amino-1-methyl-2-pyrrolecarboxamido)-1-benzamido)-2-imidazolecarboxamido]ethyl}piperidine
• 英文别名: 4-[[4-[(4-amino-1-methylpyrrole-2-carbonyl)amino]benzoyl]amino]-N-[2-(4-hydroxypiperidin-1-yl)ethyl]-1-methylimidazole-2-carboxamide
• CAS: 758727-15-0
• 化学式: C₂₅H₃₂N₈O₄
• 分子量: 508.58
• InChiKey: LFISKYQJMFPSSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-dioxa-5-thia-s-indacene-6-carboxylic acid 、 1-(2-hydroxyethyl)-4-{2-[1-methyl-4-(4-(4-amino-1-methyl-2-pyrrolecarboxamido)-1-benzamido)-2-imidazolecarboxamido]ethyl}piperidine 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.0h， 以51%的产率得到1-Methyl-4-[4-({1-methyl-4-[(thieno[2',3':4,5]benzo[1,2-d][1,3]dioxole-6-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-benzoylamino]-1H-imidazole-2-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-ethyl]-amide
  参考文献：
  名称：

  DNA Binding Ligands with Improved in Vitro and in Vivo Potency against Drug-Resistant Staphylococcus aureus

  摘要：

  Potent in vivo activity against methicillin-resistant Staphylococcus aureus (MRSA) has been difficult to achieve with previously reported DNA binding antibacterials. Herein, we describe an efficient access to a focused library of new analogues yielding compounds with improved activity in a mouse peritonitis model. The most potent molecules (14 and 19) exhibit efficacy against MRSA at ED50 values of similar to1 and similar to5 mg/kg, respectively, and display excellent in vitro activity against vancomycin-resistant S. aureus.

  DOI：

  10.1021/jm049712g
• 作为产物：
  描述：

  4-Amino-1-methyl-1H-imidazole-2-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-ethyl]-amide 在 盐酸 、 4-二甲氨基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 甲醇 为溶剂， 反应 1.5h， 生成 1-(2-hydroxyethyl)-4-{2-[1-methyl-4-(4-(4-amino-1-methyl-2-pyrrolecarboxamido)-1-benzamido)-2-imidazolecarboxamido]ethyl}piperidine
  参考文献：
  名称：

  DNA Binding Ligands with Improved in Vitro and in Vivo Potency against Drug-Resistant Staphylococcus aureus

  摘要：

  Potent in vivo activity against methicillin-resistant Staphylococcus aureus (MRSA) has been difficult to achieve with previously reported DNA binding antibacterials. Herein, we describe an efficient access to a focused library of new analogues yielding compounds with improved activity in a mouse peritonitis model. The most potent molecules (14 and 19) exhibit efficacy against MRSA at ED50 values of similar to1 and similar to5 mg/kg, respectively, and display excellent in vitro activity against vancomycin-resistant S. aureus.

  DOI：

  10.1021/jm049712g

文献信息

• DNA Binding Ligands with Improved in Vitro and in Vivo Potency against Drug-Resistant <i>Staphylococcus aureus</i>
  作者：Wenhao Hu、Roland W. Bürli、Jacob A. Kaizerman、Kirk W. Johnson、Matthew I. Gross、Mari Iwamoto、Peter Jones、Denene Lofland、Stacey Difuntorum、Hsiu Chen、Bülent Bozdogan、Peter C. Appelbaum、Heinz E. Moser

  DOI：10.1021/jm049712g

  日期：2004.8.1

  Potent in vivo activity against methicillin-resistant Staphylococcus aureus (MRSA) has been difficult to achieve with previously reported DNA binding antibacterials. Herein, we describe an efficient access to a focused library of new analogues yielding compounds with improved activity in a mouse peritonitis model. The most potent molecules (14 and 19) exhibit efficacy against MRSA at ED50 values of similar to1 and similar to5 mg/kg, respectively, and display excellent in vitro activity against vancomycin-resistant S. aureus.