8-((4-(4-allyl-2-methoxyphenoxy)butyl)oxy)-2-methylquinoline | 690970-26-4

• 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: 8-((4-(4-allyl-2-methoxyphenoxy)butyl)oxy)-2-methylquinoline
• 英文别名: 8-[4-(2-Methoxy-4-prop-2-enylphenoxy)butoxy]-2-methylquinoline
• CAS: 690970-26-4
• 化学式: C₂₄H₂₇NO₃
• 分子量: 377.483
• InChiKey: VPVNYTYRTNKYNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁香酚 、 8-(4-溴丁氧基)-2-甲基喹啉 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 49.0h， 以31%的产率得到8-((4-(4-allyl-2-methoxyphenoxy)butyl)oxy)-2-methylquinoline
  参考文献：
  名称：

  Synthesis and leishmanicidal activity of quinoline–triclosan and quinoline–eugenol hybrids

  摘要：

  In this study, hybrids 7-12 and 19-24 were synthesized via Williamson reaction of O-Quinaldine alkyl bromide plus eugenol and O-triclosan alkyl bromide plus 8-hydroxyquinaldine, respectively. Structures of the products were elucidated by spectroscopic analysis. The compounds synthesized were evaluated for antileishmanial activity against L. panamensis amastigotes and cytotoxic activity against U-937 cells. The compounds 19, 20, and 21 that are 8-hydroxyquinaldine linked to triclosan by 3, 4, and 5-carbon space, respectively, were more active against axenic amastigotes (EC (50) = 23.6, 9.7, and 4.1 mu g/ml, respectively). Compounds 19 and 21 were also active against intracellular amastigotes with EC (50) vales of 6.4 and 2.4 mu g/ml, respectively, making these compounds promising for the development of new antileishmanial drugs.Quinoline-triclosan and quinoline-eugenol hybrids were obtained using Williamson etherification reactions. Leishmanicidal activity and cytotoxicity of these compounds are reported.

  DOI：

  10.1007/s00044-011-9886-8

文献信息

• Synthesis and leishmanicidal activity of quinoline–triclosan and quinoline–eugenol hybrids
  作者：Victor Arango、Jorge J. Domínguez、Wilson Cardona、Sara M. Robledo、Diana L. Muñoz、Bruno Figadere、Jairo Sáez

  DOI：10.1007/s00044-011-9886-8

  日期：2012.11

  In this study, hybrids 7-12 and 19-24 were synthesized via Williamson reaction of O-Quinaldine alkyl bromide plus eugenol and O-triclosan alkyl bromide plus 8-hydroxyquinaldine, respectively. Structures of the products were elucidated by spectroscopic analysis. The compounds synthesized were evaluated for antileishmanial activity against L. panamensis amastigotes and cytotoxic activity against U-937 cells. The compounds 19, 20, and 21 that are 8-hydroxyquinaldine linked to triclosan by 3, 4, and 5-carbon space, respectively, were more active against axenic amastigotes (EC (50) = 23.6, 9.7, and 4.1 mu g/ml, respectively). Compounds 19 and 21 were also active against intracellular amastigotes with EC (50) vales of 6.4 and 2.4 mu g/ml, respectively, making these compounds promising for the development of new antileishmanial drugs.Quinoline-triclosan and quinoline-eugenol hybrids were obtained using Williamson etherification reactions. Leishmanicidal activity and cytotoxicity of these compounds are reported.