1,1-bis[(2-methyl-8-quinolyl)oxy]methane | 1145935-71-2

• 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: 1,1-bis[(2-methyl-8-quinolyl)oxy]methane
• 英文别名: 2-Methyl-8-[(2-methylquinolin-8-yl)oxymethoxy]quinoline
• CAS: 1145935-71-2
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: MDLIQDOOXFARNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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 、 二氯甲烷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 水 为溶剂， 以40%的产率得到1,1-bis[(2-methyl-8-quinolyl)oxy]methane
  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

• QUINOLINE DERIVATIVES AS ANTI-CANCER AGENTS
  申请人：TANG Johnny Cheuk-on

  公开号：US20120165370A1

  公开（公告）日：2012-06-28

  Quinoline derivatives showing anticancer activities against cancer cell lines of hepatocellular carcinoma (Hep3B), lung carcinoma (A549), esophageal squamous cell carcinoma (HKESC-1, HKESC-4 and KYSE150). The quinoline derivatives have a backbone structure of the following formulas:

  喹啉衍生物显示抗癌活性，针对肝细胞癌（Hep3B）、肺癌（A549）、食道鳞状细胞癌（HKESC-1、HKESC-4和KYSE150）细胞系。这些喹啉衍生物具有以下结构的骨架式样：
• US9493419B2
  申请人：——

  公开号：US9493419B2

  公开（公告）日：2016-11-15
• 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.