(R)-2-nitro-7-(2-phenoxyethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-2-nitro-7-(2-phenoxyethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• 英文别名: (7R)-2-nitro-7-(2-phenoxyethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: GGIOMBMRULRTCW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,5-戊三醇 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 四丁基碘化铵 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 三苯基膦 、 原甲酸三甲酯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.5h， 生成 (R)-2-nitro-7-(2-phenoxyethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
  参考文献：
  名称：

  Synthesis and anti-tubercular activity of 2-nitroimidazooxazines with modification at the C-7 position as PA-824 analogs

  摘要：

  Tuberculosis (TB) is a major global health problem, and new drug targets and scaffolds need to be identified to combat the emergence of drug resistant TB.The nitroimidazooxazine PA-824 represents a new class of bio-reductive drug to treat TB. In this study we report a 2-nitroimidazooxazine derivative with modification at the C-7 position that exhibited better activity than PA-824 against Mycobacterium tuberculosis (Mtb) H37Rv strain in vitro. From 7a as a key intermediate, we functionalized with benzyl ether (8), phenyl ether (9), benzyl carbonate (10) and benzyl carbamate (11). Among the 23 compounds produced, 8a-R (MIC = 0.078 mu M) with trifluoromethoxy benzyl group was 5-fold more potent than PA-824 (MIC = 0.390 mu M) in the in vitro assays against the wild-type Mtb, and the phenyl ether compound 9g-R (MIC = 0.050 mu M) exhibited the most potent antimycobacterial activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.060