9-(3,4-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid isopropyl amide | 1450605-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 9-(3,4-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid isopropyl amide
• 英文别名: (2E,4E,8E)-9-(1,3-benzodioxol-5-yl)-N-propan-2-ylnona-2,4,8-trienamide
• CAS: 1450605-03-4
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: BDEUHVWQXPMBBZ-FCGWLDPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 9-(3,4-methylenedioxyphenyl)nona-2E,4E,8E-trienoate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 9-(3,4-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid isopropyl amide
  参考文献：
  名称：

  Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells

  摘要：

  In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the tested compounds, an amide composed of 9-(3',4'-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover, the amide with the n-pentyl amine moiety significantly increased the uptake of 2-deoxyglucose into the cells, and also increased the mRNA levels of adiponectin, peroxisome proliferator-activated receptor gamma 2 (PPAR gamma 2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) alpha and beta in a similar manner as the PPAR gamma agonist troglitazone, although it had less agonistic activity against PPAR gamma. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.101

文献信息

• Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells
  作者：Ahmed Aboul-Fotouh Mourad、Seikou Nakamura、Tsubasa Ueno、Takahiro Minami、Takanari Yagi、Haruka Yasue、Ryoko Komatsu、Masayuki Yoshikawa、Ashraf Mohamed Taye、Mohamed Ahmed El-Moselhy、Mohamed Montaser Khalifa、Hisashi Matsuda

  DOI：10.1016/j.bmcl.2013.06.101

  日期：2013.9

  In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the tested compounds, an amide composed of 9-(3',4'-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover, the amide with the n-pentyl amine moiety significantly increased the uptake of 2-deoxyglucose into the cells, and also increased the mRNA levels of adiponectin, peroxisome proliferator-activated receptor gamma 2 (PPAR gamma 2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) alpha and beta in a similar manner as the PPAR gamma agonist troglitazone, although it had less agonistic activity against PPAR gamma. (C) 2013 Elsevier Ltd. All rights reserved.