3-庚基-4-羟基-7-甲氧基-2-甲基喹啉 | 4939-34-8

• 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
• 中文名称: 3-庚基-4-羟基-7-甲氧基-2-甲基喹啉
• 英文名称: endochin
• 英文别名: 3-Heptyl-4-hydroxy-7-methoxy-2-methylquinoline；3-heptyl-7-methoxy-2-methyl-1H-quinolin-4-one
• CAS: 4939-34-8
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: BCZRFDKLLBFOHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  218.5-219 °C
• 沸点：
  429.8±40.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-庚基-4-羟基-7-甲氧基-2-甲基喹啉 在 氢碘酸 、 溶剂黄146 作用下， 生成 3-heptyl-2-methyl-quinoline-4,7-diol
  参考文献：
  名称：

  Salzer et al., Chemische Berichte, 1948, vol. 81, p. 12,17

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基壬-2-烯酸乙酯 在 乙醚 、 镍 作用下， 生成 3-庚基-4-羟基-7-甲氧基-2-甲基喹啉
  参考文献：
  名称：

  Leonard; Herbrandson; Van Heyningen, Journal of the American Chemical Society, 1946, vol. 68, p. 1281

  摘要：

  DOI：

文献信息

• Endochin Optimization: Structure−Activity and Structure−Property Relationship Studies of 3-Substituted 2-Methyl-4(1<i>H</i>)-quinolones with Antimalarial Activity
  作者：R. Matthew Cross、Andrii Monastyrskyi、Tina S. Mutka、Jeremy N. Burrows、Dennis E. Kyle、Roman Manetsch

  DOI：10.1021/jm1007903

  日期：2010.10.14

  Since the 1940s endochin and analogues thereof were known to be causal prophylactic and potent erythrocytic stage agents in avian models. Preliminary screening in a current in vitro assay identified several 4(1H)-quinolones with nanomolar EC(50) against erythrocytic stages of mullidrug resistant W2 and TM90-C2B isolates of Plasmodium folciparum. Follow-up structure activity relationship (SAR) studies on 4(1H)-quinolone analogues identified several key features for biological activity. Nevertheless, structure property relationship (SPR) studies conducted in parallel revealed that 4(1H)-quinolone analogues are limited by poor solubilities and rapid microsomal degradations. To improve the overall efficacy, multiple 4(1H)-quinolone series with varying substituents on the benzenoid quinolone ring and/or the 3-position were synthesized and tested for in vitro antimalarial activity. Several structurally diverse 6-chloro-2-methyl-7-methoxy-4(1H)-quinolones with EC(50) in the low nanomolar range against the clinically relevant isolates W2 and TM90-C2B were identified with improved physicochemical properties while maintaining little to no cross-resistance with atovaquone.
• Stephen et al., Journal of the Chemical Society, 1947, p. 1034,1037
  作者：Stephen et al.

  DOI：——

  日期：——
• Salzer et al., Chemische Berichte, <hi>1848</hi>, vol. 81, p. 12,19
  作者：Salzer et al.

  DOI：——

  日期：——
• Salzer et al., Chemische Berichte, 1948, vol. 81, p. 12,17
  作者：Salzer et al.

  DOI：——

  日期：——
• Leonard; Herbrandson; Van Heyningen, Journal of the American Chemical Society, 1946, vol. 68, p. 1281
  作者：Leonard、Herbrandson、Van Heyningen

  DOI：——

  日期：——