N-[(S)-3-(4H,6H-5-Oxa-10b-aza-benzo[e]azulen-8-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide | 862275-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-[(S)-3-(4H,6H-5-Oxa-10b-aza-benzo[e]azulen-8-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
• 英文别名: N-[[(5S)-3-(4,6-dihydropyrrolo[1,2-a][4,1]benzoxazepin-8-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 862275-59-0
• 化学式: C₁₈H₁₉N₃O₄
• 分子量: 341.367
• InChiKey: QXXKVYNZPDIMSW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(S)-3-(4H,6H-5-Oxa-10b-aza-benzo[e]azulen-8-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以82%的产率得到
  参考文献：
  名称：

  Substituent activity relationship studies on new azolo benzoxazepinyl oxazolidinones

  摘要：

  In an effort to discover potent antibacterials based on the entropically favored 'bioactive conformation' approach, a series of novel tricyclic molecules mimicking the conformationally constrained structure of Linezolid is reported. Based on the initial tricyclic molecule 1, the benzazepine derivative 2 was designed where the tricyclic structure had more flexibility around C-N bond compared to 1. While, the molecule 2 was less active, the molecule 3 showed promising antibacterial activity presumably after having obtained rigidity due to pyrrole ring. The syntheses, SAR studies, and evaluation of 3 as a lead compound are reported.

  DOI：

  10.1016/j.bmc.2006.07.040
• 作为产物：
  描述：

  2-氨基-5-硝基苯甲酸甲酯 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 sodium azide 、 ammonium formate 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.17h， 生成 N-[(S)-3-(4H,6H-5-Oxa-10b-aza-benzo[e]azulen-8-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
  参考文献：
  名称：

  Substituent activity relationship studies on new azolo benzoxazepinyl oxazolidinones

  摘要：

  In an effort to discover potent antibacterials based on the entropically favored 'bioactive conformation' approach, a series of novel tricyclic molecules mimicking the conformationally constrained structure of Linezolid is reported. Based on the initial tricyclic molecule 1, the benzazepine derivative 2 was designed where the tricyclic structure had more flexibility around C-N bond compared to 1. While, the molecule 2 was less active, the molecule 3 showed promising antibacterial activity presumably after having obtained rigidity due to pyrrole ring. The syntheses, SAR studies, and evaluation of 3 as a lead compound are reported.

  DOI：

  10.1016/j.bmc.2006.07.040

文献信息

• Substituent activity relationship studies on new azolo benzoxazepinyl oxazolidinones
  作者：Jagattaran Das、M. Sitaram Kumar、D. Subrahmanyam、T.V.R.S. Sastry、C. Prasad Narasimhulu、C.V. Laxman Rao、M. Kannan、M. Roshaiah、Riti Awasthi、Santosh N. Patil、H.M. Sarnaik、N.V.S. Rao Mamidi、N. Selvakumar、Javed Iqbal

  DOI：10.1016/j.bmc.2006.07.040

  日期：2006.12

  In an effort to discover potent antibacterials based on the entropically favored 'bioactive conformation' approach, a series of novel tricyclic molecules mimicking the conformationally constrained structure of Linezolid is reported. Based on the initial tricyclic molecule 1, the benzazepine derivative 2 was designed where the tricyclic structure had more flexibility around C-N bond compared to 1. While, the molecule 2 was less active, the molecule 3 showed promising antibacterial activity presumably after having obtained rigidity due to pyrrole ring. The syntheses, SAR studies, and evaluation of 3 as a lead compound are reported.