(E)-3,7-dimethylocta-2,6-dienyl 8-hydroxy-4-methoxyquinoline-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: (E)-3,7-dimethylocta-2,6-dienyl 8-hydroxy-4-methoxyquinoline-2-carboxylate
• 英文别名: [(2E)-3,7-dimethylocta-2,6-dienyl] 8-hydroxy-4-methoxyquinoline-2-carboxylate
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: QKMNWTSEZHSHRQ-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3,7-dimethylocta-2,6-dienyl 8-hydroxy-4-methoxyquinoline-2-carboxylate 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (E)-3,7-dimethylocta-2,6-dienyl 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
• 作为产物：
  描述：

  8-羟基-4-甲氧基喹啉-2-羧酸甲酯 在 水 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (E)-3,7-dimethylocta-2,6-dienyl 8-hydroxy-4-methoxyquinoline-2-carboxylate
  参考文献：
  名称：

  JP6348845

  摘要：

  公开号：

文献信息

• JP6348845
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] PRENYLOXYQUINOLINE CARBOXYLIC-ACID DERIVATIVE<br/>[FR] DÉRIVÉ D'ACIDE PRÉNYLOXYQUINOLINE-CARBOXYLIQUE
  申请人：FUKUSHIMA MEDICAL UNIVERSITY

  公开号：WO2014061647A1

  公开（公告）日：2014-04-24

  　生体に対する副作用が少ない脱共役作用及び／又は免疫抑制作用を有する化合物を開発し、その化合物を有効成分とする体重増加抑制剤又は免疫抑制剤を提供することを課題とする。　以下の一般式（I）で示される化合物又はその塩を提供する。［式中、R1は、水素原子（H）、C5、C10、C15若しくはC20のプレニル基を表し、R2は、C1～C10の直鎖状若しくは分岐状のアルキル基、又はC5、C10、C15若しくはC20のプレニル基を表し、R3及びR4は、それぞれ独立してC5、C10、C15、若しくはC20のプレニル基（ただし、R1がH及びR2がメチル基のときのC5のプレニル基を除く）、又はイソペンチル基を表す］
• 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.