methyl 4-methoxy-8-(3-methylbut-2-enyloxy)quinoline-2-carboxylate

• 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: methyl 4-methoxy-8-(3-methylbut-2-enyloxy)quinoline-2-carboxylate
• 英文别名: Methyl 4-methoxy-8-(3-methylbut-2-enoxy)quinoline-2-carboxylate；methyl 4-methoxy-8-(3-methylbut-2-enoxy)quinoline-2-carboxylate
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: UANPBWIAUURWCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,8-二羟基喹啉-2-甲酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 4-methoxy-8-(3-methylbut-2-enyloxy)quinoline-2-carboxylate
  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.