8-(4-溴丁氧基)-2-甲基喹啉 | 1099130-86-5

• 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
• 中文名称: 8-(4-溴丁氧基)-2-甲基喹啉
• 英文名称: 8-(4-Bromobutoxy)-2-methylquinoline
• CAS: 1099130-86-5
• 化学式: C₁₄H₁₆BrNO
• mdl: MFCD11647856
• 分子量: 294.191
• InChiKey: MKYMEEKOUZLCIS-UHFFFAOYSA-N

物化性质

• 沸点：
  403.9±35.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,4-二溴丁烷 、 8-羟基喹哪啶 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 1,4-bis[(2-methyl-8-quinolyl)oxy]butane 、 8-(4-溴丁氧基)-2-甲基喹啉
  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 NEW BIS-ALKYLQUINOLINES
  作者：WILSON CARDONA、VICTOR ARANGO、JORGE J DOMÍNGUEZ、SARA M ROBLEDO、DIANA L MUÑOZ、BRUNO FIGADERE、IVAN D VELEZ、JAIRO SÁEZ

  DOI：10.4067/s0717-97072013000200014

  日期：——
• 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.