4-methyl-3H-oxazolo[4,5-c]quinoline-2-one hydrobromide | 1075198-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methyl-3H-oxazolo[4,5-c]quinoline-2-one hydrobromide
• 英文别名: 4-methyl-3H-[1,3]oxazolo[4,5-c]quinolin-2-one;hydrobromide
• CAS: 1075198-67-2
• 化学式: BrH*C₁₁H₈N₂O₂
• 分子量: 281.109
• InChiKey: GBZLEKMOFNCMGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-bromocarbonylamino-2-methyl-1H-quinoline-4-one 在 二甲基亚砜 作用下， 生成 4-methyl-3H-oxazolo[4,5-c]quinoline-2-one hydrobromide
  参考文献：
  名称：

  Semisynthesis and Antiplasmodial Activity of the Quinoline Alkaloid Aurachin E

  摘要：

  A one-step synthesis of the rare aurachin E (1) from the easily accessible aurachin C (2) and cyanogen bromide is described. 3-Bromocarbamoylquinoline (5) is formed in a side reaction with concomitant loss of the 3-farnesyl residue. In an alternative approach, aurachin D (3) was reacted with phosgene and sodium azide to form the imidazolone ring of 1 via N-acylation. Unexpectedly, the initial reaction occurred at the carbonyl group of 3 to give 1H-pyrrolo[3,2-c]quinoline 4. The reaction sequence represents a novel route to this type of compound. Aurachin E, contrary to other aurachins, combines a high in vitro antiplasmodial activity with low cytotoxicity and absence of mitochondrial respiratory inhibition.

  DOI：

  10.1021/np8004612