1,5-bis[(2-methyl-8-quinolyl)oxy]pentane | 1026668-03-0

• 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: 1,5-bis[(2-methyl-8-quinolyl)oxy]pentane
• 英文别名: 2-Methyl-8-[5-(2-methylquinolin-8-yl)oxypentoxy]quinoline
• CAS: 1026668-03-0
• 化学式: C₂₅H₂₆N₂O₂
• 分子量: 386.494
• InChiKey: CPKBZWNWVLFYCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-羟基喹哪啶 、 1,5-二氯戊烷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 水 为溶剂， 以32%的产率得到1,5-bis[(2-methyl-8-quinolyl)oxy]pentane
  参考文献：
  名称：

  Phase transfer catalyzed synthesis of bis-quinolines: Antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation

  摘要：

  A one-pot synthesis of some novel bis-quinolines has been achieved under phase transfer catalyzed conditions using 8-hydroxy quinoline derivatives as substrates. The synthesized analogues were evaluated for antileishmanial activity against Leishmania donovani promastigotes and amastigotes. The entire bis-quinolines showed efficacy in both in vitro and in vivo studies. Compound 5 (1,1-bis-[(5-chloro-8-quinolyl)oxy] methane) exhibited the most significant activity. Compounds 4 (1,1-bis-[(8-quinolyl)oxylmethane) and 9 (1,5-bis-[(2-methyl-8-quinolyl)oxy] pentane) also demonstrated significant leishmanicidal efficacy against established visceral leishmaniasis in BALB/c model. Ultrastructural studies of promastigotes treated with compound 5, demonstrated membrane blebbing, chromatin condensation and vacuolization in the parasites and the flagellated parasites became round shaped after treatment. Moreover, in vitro antibacterial activity of compound 5 against several bacterial strains revealed its promising efficacy. The findings suggested that 1,1-bis-[(5-chloro-8-quinolyl)oxy] methane (5) is a bright candidate to be considered as lead compound for leishmanicidal drug. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.014

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.
• Facile synthesis of seven to nine-membered-fused tricyclic quinolones and quinolinium salts under phase transfer catalyzed conditions
  作者：Priyankar Paira、Abhijit Hazra、Krishnendu B. Sahu、Sukdeb Banerjee、Nirup B. Mondal、Niranjan P. Sahu、Manuela Weber、Peter Luger

  DOI：10.1016/j.tet.2008.02.048

  日期：2008.4

  Phase transfer catalyzed one-pot syntheses of fused oxazepino, oxazocino, and oxazonino quinolinium cations and quinolones were achieved from 8-hydroxy quinoline derivatives with 1,omega-dihaloalkanes. Structures of all the products were elucidated by spectroscopic analysis. Single crystal X-ray crystallographic analysis of three compounds and graphical superposition of the structures indicate that products having seven-membered ring are less planar compared to the product having eight-membered ring. (c) 2008 Elsevier Ltd. All rights reserved.
• Phase transfer catalyzed synthesis of bis-quinolines: Antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation
  作者：Partha Palit、Priyankar Paira、Abhijit Hazra、Sukdeb Banerjee、Asish Das Gupta、Sujata G. Dastidar、Nirup B. Mondal

  DOI：10.1016/j.ejmech.2008.04.014

  日期：2009.2

  A one-pot synthesis of some novel bis-quinolines has been achieved under phase transfer catalyzed conditions using 8-hydroxy quinoline derivatives as substrates. The synthesized analogues were evaluated for antileishmanial activity against Leishmania donovani promastigotes and amastigotes. The entire bis-quinolines showed efficacy in both in vitro and in vivo studies. Compound 5 (1,1-bis-[(5-chloro-8-quinolyl)oxy] methane) exhibited the most significant activity. Compounds 4 (1,1-bis-[(8-quinolyl)oxylmethane) and 9 (1,5-bis-[(2-methyl-8-quinolyl)oxy] pentane) also demonstrated significant leishmanicidal efficacy against established visceral leishmaniasis in BALB/c model. Ultrastructural studies of promastigotes treated with compound 5, demonstrated membrane blebbing, chromatin condensation and vacuolization in the parasites and the flagellated parasites became round shaped after treatment. Moreover, in vitro antibacterial activity of compound 5 against several bacterial strains revealed its promising efficacy. The findings suggested that 1,1-bis-[(5-chloro-8-quinolyl)oxy] methane (5) is a bright candidate to be considered as lead compound for leishmanicidal drug. (c) 2008 Elsevier Masson SAS. All rights reserved.