3-(chloromethyl)isoxazole-4-carboxylic acid ethyl ester | 1379165-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(chloromethyl)isoxazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-(chloromethyl)-1,2-oxazole-4-carboxylate
• CAS: 1379165-76-0
• 化学式: C₇H₈ClNO₃
• 分子量: 189.598
• InChiKey: RIKJYEXUKWIYRW-UHFFFAOYSA-N

物化性质

• 沸点：
  318.5±32.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-氯乙醛肟 、 丙炔酸乙酯 在 sodium hypochlorite 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到3-(氯甲基)异恶唑-5-羧酸乙酯
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 mu M, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 mu M concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

  DOI：

  10.1021/jm900003c