N-(trans-1-cinnamylpiperazin-1-yl)-(13S)-15-acetoxylabd-8-(17)-en-19-methyl ester | 1388727-71-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(trans-1-cinnamylpiperazin-1-yl)-(13S)-15-acetoxylabd-8-(17)-en-19-methyl ester
• 英文别名: methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(3S)-3-methyl-5-[2-[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]acetyl]oxypentyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 1388727-71-6
• 化学式: C₃₆H₅₄N₂O₄
• 分子量: 578.836
• InChiKey: GSYALSJFNZWMOG-BFVXCJDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1S,4aR,5S,8aR)-decahydro-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylenenaphthalene-1-carboxylic acid 在 吡啶 、 potassium carbonate 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 N-(trans-1-cinnamylpiperazin-1-yl)-(13S)-15-acetoxylabd-8-(17)-en-19-methyl ester
  参考文献：
  名称：

  Synthesis of novel imbricatolic acid analogues via insertion of N-substituted piperazine at C-15/C-19 positions, displaying glucose uptake stimulation in L6 skeletal muscle cells

  摘要：

  A new class of N-substituted piperazine analogues of imbricatolic acid have been designed and synthesized by using the appropriate synthetic routes in excellent yield. All synthesised compounds were screened for their in vitro glucose uptake stimulatory activity. Among them compounds 4b, 4e, 8b, and 8e triggered L6 skeletal muscle cells for glucose uptake at 54.73%, 40.79%, 40.90%, and 39.55% stimulation, respectively. Compound 4b has emerged as important lead compound showing potential antidiabetic activity. Illustration about their synthesis and in vitro glucose uptake activity is described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.097

文献信息

• Synthesis of novel imbricatolic acid analogues via insertion of N-substituted piperazine at C-15/C-19 positions, displaying glucose uptake stimulation in L6 skeletal muscle cells
  作者：Mohammad Faheem Khan、Padam Kumar、Jyotsana Pandey、Arvind Kumar Srivastava、Akhilesh Kumar Tamrakar、Rakesh Maurya

  DOI：10.1016/j.bmcl.2012.05.097

  日期：2012.7

  A new class of N-substituted piperazine analogues of imbricatolic acid have been designed and synthesized by using the appropriate synthetic routes in excellent yield. All synthesised compounds were screened for their in vitro glucose uptake stimulatory activity. Among them compounds 4b, 4e, 8b, and 8e triggered L6 skeletal muscle cells for glucose uptake at 54.73%, 40.79%, 40.90%, and 39.55% stimulation, respectively. Compound 4b has emerged as important lead compound showing potential antidiabetic activity. Illustration about their synthesis and in vitro glucose uptake activity is described. (C) 2012 Elsevier Ltd. All rights reserved.