[(3R,4S,5R,6R)-6-[3-[[3-[[4-(dimethylamino)butanoyl-methylamino]methyl]-4-hydroxy-5-(3-methylbut-2-enyl)benzoyl]amino]-4-hydroxy-8-methyl-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate | 1337988-16-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: [(3R,4S,5R,6R)-6-[3-[[3-[[4-(dimethylamino)butanoyl-methylamino]methyl]-4-hydroxy-5-(3-methylbut-2-enyl)benzoyl]amino]-4-hydroxy-8-methyl-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
• CAS: 1337988-16-5
• 化学式: C₃₉H₅₂N₄O₁₂
• 分子量: 768.861
• InChiKey: JMQCSPOOUQDYJB-ZNHXKFHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  220
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  新生霉素 在 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 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 [(3R,4S,5R,6R)-6-[3-[[3-[[4-(dimethylamino)butanoyl-methylamino]methyl]-4-hydroxy-5-(3-methylbut-2-enyl)benzoyl]amino]-4-hydroxy-8-methyl-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate
  参考文献：
  名称：

  Mannich reaction derivatives of novobiocin with modulated physiochemical properties and their antibacterial activities

  摘要：

  Synthetic derivatives of the natural product antibiotic novobiocin were synthesized in order to improve their physiochemical properties. A Mannich reaction was used to introduce new side chains at a solventexposed position of the molecule, and a diverse panel of functional groups was evaluated at this position. Novobiocin and the new derivatives were tested for their binding to gyrase B and their antibacterial activities against Staphylococcus aureus, Mycobacterium tuberculosis, Francisella tularensis and Escherichia coli. While the new derivatives still bound the gyrase B protein potently (0.07-1.8 mu M, IC50),they had significantly less antibacterial activity. Two compounds were identified with increased antibacterial activity against M. tuberculosis, with a minimum inhibitory concentration of 2.5 mu g/ml. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.035

文献信息

• Mannich reaction derivatives of novobiocin with modulated physiochemical properties and their antibacterial activities
  作者：Arlyn Tambo-ong、Sidharth Chopra、Bryan T. Glaser、Karen Matsuyama、Tran Tran、Peter B. Madrid

  DOI：10.1016/j.bmcl.2011.08.035

  日期：2011.10

  Synthetic derivatives of the natural product antibiotic novobiocin were synthesized in order to improve their physiochemical properties. A Mannich reaction was used to introduce new side chains at a solventexposed position of the molecule, and a diverse panel of functional groups was evaluated at this position. Novobiocin and the new derivatives were tested for their binding to gyrase B and their antibacterial activities against Staphylococcus aureus, Mycobacterium tuberculosis, Francisella tularensis and Escherichia coli. While the new derivatives still bound the gyrase B protein potently (0.07-1.8 mu M, IC50),they had significantly less antibacterial activity. Two compounds were identified with increased antibacterial activity against M. tuberculosis, with a minimum inhibitory concentration of 2.5 mu g/ml. (C) 2011 Elsevier Ltd. All rights reserved.