(13S)-15-acetoxylabd-8-(17)-en-19-oic acid

• 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: (13S)-15-acetoxylabd-8-(17)-en-19-oic acid
• 英文别名: (13S)-15-acetoxylabd-8(17)-en-19-oic acid；13S-15-acetoxylabd-8(17)-en-18-oic acid；15-acetoxy-imbricatolic acid；15-acetoxyimbricatolic acid；(1S,4aR,5S,8aR)-5-[(3S)-5-acetyloxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: AAPGEKMDLXBUBL-ZGNLYJAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (13S)-15-acetoxylabd-8-(17)-en-19-oic acid 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 (13S)-15-(α-bromo)-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
• 作为产物：
  描述：

  乙酸酐 、 (1S,4aR,5S,8aR)-decahydro-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylenenaphthalene-1-carboxylic acid 在 吡啶 作用下， 以10 mg的产率得到(13S)-15-acetoxylabd-8-(17)-en-19-oic acid
  参考文献：
  名称：

  Three Labdane-Type Diterpenes from the Bark of Juniperus formosana HAY. var. concolor HAY.

  摘要：

  从杜松（Juniperus formosana HAY.var.concolor HAY）树皮中发现了三种新的拉布丹型二萜，即(13S)-15-羟基拉布丹-8(17)-烯-19-酸、(13S)-15-乙酰氧基拉布丹-8(17)-烯-19-酸和(13S)-15-十八碳酰氧基拉布丹-8(17)-烯-19-酸，以及一种已知化合物对映体奥利韦酸。根据光谱数据和化学变化阐明了它们的结构。

  DOI：

  10.1248/cpb.44.1242

文献信息

• Three Labdane-Type Diterpenes from the Bark of Juniperus formosana HAY. var. concolor HAY.
  作者：Yueh-Hsiung KUO、Ming-Tsang YU

  DOI：10.1248/cpb.44.1242

  日期：——

  Three new labdane-type diterpenes, (13S)-15-hydroxylabd-8(17)-en-19-oic acid, (13S)-15-acetoxylabd-8(17)-en-19-oic acid, and (13S)-15-octadecanoyloxylabd-8(17)-en-19-oic acid, together with one known compound, enantio-oliveric acid, were found from the bark of Juniperus formosana HAY. var. concolor HAY. Their structures were elucidated on the basis of spectral data and chemical transformation.

  从杜松（Juniperus formosana HAY.var.concolor HAY）树皮中发现了三种新的拉布丹型二萜，即(13S)-15-羟基拉布丹-8(17)-烯-19-酸、(13S)-15-乙酰氧基拉布丹-8(17)-烯-19-酸和(13S)-15-十八碳酰氧基拉布丹-8(17)-烯-19-酸，以及一种已知化合物对映体奥利韦酸。根据光谱数据和化学变化阐明了它们的结构。
• 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.