(1S,4aR,5S,8aR)-decahydro-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylenenaphthalene-1-carboxylic acid | 4742-38-5

• 物质功能分类: 天然产物 - 萜类
• 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: (1S,4aR,5S,8aR)-decahydro-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylenenaphthalene-1-carboxylic acid
• 英文别名: (13S)-15-hydroxylabd-8(17)-en-19-oic acid；13S-15-hydroxylabd-8(17)-en-18-oic acid；15-hydroxy-labd-8(17)-en-19-oic acid；15-hydroxylabd-8(17)-en-19-oic acid；imbricatoloic acid；imbricatolic acid；(1S,4aR,5S,8aR)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 4742-38-5；5095-36-3；47255-93-6；103664-45-5；138125-20-9；140145-43-3；141039-88-5；6832-60-6
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: NSRKLZRKJJQJLD-BEUFEYIVSA-N

物化性质

• 熔点：
  102-105 °C
• 沸点：
  446.7±38.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

南洋杉酸是柏子仁的一种成分，具有用于治疗神经退行性疾病的功效。

反应信息

• 作为反应物：
  描述：

  (1S,4aR,5S,8aR)-decahydro-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylenenaphthalene-1-carboxylic acid 在 吡啶 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(1-acetoxypiperazin-1-yl)-(13S)-15-acetoxylabd-8-(17)-en-19-amide
  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

• 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.