4-methoxy-N-(3-methylbut-2-enyl)-8-(3-methylbut-2-enyloxy)quinoline-2-carboxamide

• 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: 4-methoxy-N-(3-methylbut-2-enyl)-8-(3-methylbut-2-enyloxy)quinoline-2-carboxamide
• 英文别名: 4-methoxy-8-(3-methylbut-2-enoxy)-N-(3-methylbut-2-enyl)quinoline-2-carboxamide
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: XFONOLRYFQHWGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-羟基-4-甲氧基喹啉-2-羧酸甲酯 在 potassium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4-methoxy-N-(3-methylbut-2-enyl)-8-(3-methylbut-2-enyloxy)quinoline-2-carboxamide
  参考文献：
  名称：

  Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities

  摘要：

  Mitochondrial uncoupling is one of the therapeutic strategies used to control energy metabolism in various metabolic diseases and in obesity. Ppc-1 (1), a prenylated quinolinecarboxylic acid isolated from cellular slime molds, shows uncoupling activity in vitro and anti-obesity activity in vivo. In this study, we synthesized Ppc-1 (1) and its derivatives, and revealed the structure-activity relationship of uncoupling activities. The triprenylated compound 18 showed mitochondrial uncoupling activity that was more potent than that of Ppc-1 (1). Compound 18 also suppressed weight gain in mice without undesired effects such as lesions on tissues. These results indicate that compound 18 could be used as a seed compound for new anti-obesity drugs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.024

文献信息

• Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities
  作者：Haruhisa Kikuchi、Toshiyuki Suzuki、Masato Ogura、Miwako K. Homma、Yoshimi Homma、Yoshiteru Oshima

  DOI：10.1016/j.bmc.2014.11.024

  日期：2015.1

  Mitochondrial uncoupling is one of the therapeutic strategies used to control energy metabolism in various metabolic diseases and in obesity. Ppc-1 (1), a prenylated quinolinecarboxylic acid isolated from cellular slime molds, shows uncoupling activity in vitro and anti-obesity activity in vivo. In this study, we synthesized Ppc-1 (1) and its derivatives, and revealed the structure-activity relationship of uncoupling activities. The triprenylated compound 18 showed mitochondrial uncoupling activity that was more potent than that of Ppc-1 (1). Compound 18 also suppressed weight gain in mice without undesired effects such as lesions on tissues. These results indicate that compound 18 could be used as a seed compound for new anti-obesity drugs. (C) 2014 Elsevier Ltd. All rights reserved.