ethyl 3-(6-quinolylamino)crotonate | 121810-79-5

• 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: ethyl 3-(6-quinolylamino)crotonate
• 英文别名: ethyl 3-(quinolin-6-ylamino)but-2-enoate
• CAS: 121810-79-5
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: YUEGCEFWAHDXIF-UHFFFAOYSA-N

物化性质

• 沸点：
  413.7±41.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(6-quinolylamino)crotonate 在 盐酸 、 sodium cyanoborohydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 15.0h， 生成 3-(6-quinolylamino)butyric acid hydrazide
  参考文献：
  名称：

  Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogs

  摘要：

  N-(2-Naphthyl)glycine hydrazide analogues were synthesized and tested for possible in vitro antitubercular activity. N-(2-Naphthyl)alanine hydrazide (3), N-methyl-N-(2-naphthyl)glycine hydrazide (5), N-(6-methoxy-2-naphthyl)glycine hydrazide (7), and 3-(2-naphthylamino)butyric acid hydrazide (23) showed potent inhibitory action against Mycobacterium tuberculosis H37Rv in Youman's medium at concentrations ranging from 0.5 to 10.0 micrograms/mL. These compounds showed significant inhibitory action against isonicotinic acid hydrazide and streptomycin-resistant strains of M. tuberculosis. N-(6-Quinolyl)glycine hydrazide (18) and 3-(2-quinolylamino)butyric acid hydrazide (24), which are bioisosteres of compounds 1 and 23, showed loss of antitubercular activity at low concentrations.

  DOI：

  10.1021/jm00131a002
• 作为产物：
  描述：

  6-氨基喹啉 、 乙酰乙酸乙酯 在 盐酸 作用下， 反应 96.0h， 以78.1%的产率得到ethyl 3-(6-quinolylamino)crotonate
  参考文献：
  名称：

  Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogs

  摘要：

  N-(2-Naphthyl)glycine hydrazide analogues were synthesized and tested for possible in vitro antitubercular activity. N-(2-Naphthyl)alanine hydrazide (3), N-methyl-N-(2-naphthyl)glycine hydrazide (5), N-(6-methoxy-2-naphthyl)glycine hydrazide (7), and 3-(2-naphthylamino)butyric acid hydrazide (23) showed potent inhibitory action against Mycobacterium tuberculosis H37Rv in Youman's medium at concentrations ranging from 0.5 to 10.0 micrograms/mL. These compounds showed significant inhibitory action against isonicotinic acid hydrazide and streptomycin-resistant strains of M. tuberculosis. N-(6-Quinolyl)glycine hydrazide (18) and 3-(2-quinolylamino)butyric acid hydrazide (24), which are bioisosteres of compounds 1 and 23, showed loss of antitubercular activity at low concentrations.

  DOI：

  10.1021/jm00131a002