(3Z)-7-chloro-3-[2-(2-chlorophenyl)-2-oxoethylidene]-4H-1,4-benzoxazin-2-one | 1257269-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (3Z)-7-chloro-3-[2-(2-chlorophenyl)-2-oxoethylidene]-4H-1,4-benzoxazin-2-one
• CAS: 1257269-14-9
• 化学式: C₁₆H₉Cl₂NO₃
• 分子量: 334.158
• InChiKey: PEOOXONEKBQCAK-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 2-hydroxy-4-oxo-4-(2'-chlorophenyl)-but-2-enoate 、 2-氨基-5-氯苯酚 在 溶剂黄146 作用下， 反应 2.0h， 生成 (3Z)-7-chloro-3-[2-(2-chlorophenyl)-2-oxoethylidene]-4H-1,4-benzoxazin-2-one
  参考文献：
  名称：

  Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis

  摘要：

  Menaquinone is an essential component of the electron transport chain in many pathogens and consequently enzymes in the menaquinone biosynthesis pathway are potential drug targets for the development of novel antibacterial agents. In order to identify leads that target MenB, the 1,4-dihydroxy-2-naphthoyl-CoA synthase from Mycobacterium tuberculosis, a high-throughput screen was performed. Several 1,4-benzoxazines were identified in this screen and subsequent SAR studies resulted in the discovery of compounds with excellent antibacterial activity against M. tuberculosis H37Rv with MIC values as low as 0.6 mu g/ml. The 1,4-benzoxazine scaffold is thus a promising foundation for the development of antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.076

文献信息

• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis
  作者：Xiaokai Li、Nina Liu、Huaning Zhang、Susan E. Knudson、Richard A. Slayden、Peter J. Tonge

  DOI：10.1016/j.bmcl.2010.08.076

  日期：2010.11

  Menaquinone is an essential component of the electron transport chain in many pathogens and consequently enzymes in the menaquinone biosynthesis pathway are potential drug targets for the development of novel antibacterial agents. In order to identify leads that target MenB, the 1,4-dihydroxy-2-naphthoyl-CoA synthase from Mycobacterium tuberculosis, a high-throughput screen was performed. Several 1,4-benzoxazines were identified in this screen and subsequent SAR studies resulted in the discovery of compounds with excellent antibacterial activity against M. tuberculosis H37Rv with MIC values as low as 0.6 mu g/ml. The 1,4-benzoxazine scaffold is thus a promising foundation for the development of antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.