podocarpic acid benzyl ester | 783321-36-8

• 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: podocarpic acid benzyl ester
• 英文别名: benzyl podocarpate；(1S,4aS,10aR)-6-Hydroxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid benzyl ester；benzyl (1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 783321-36-8
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: KMEJLXYWBXIHMZ-JRFVFWCSSA-N

物化性质

• 沸点：
  498.3±45.0 °C(predicted)
• 密度：
  1.145±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴丙酸 、 podocarpic acid benzyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以31%的产率得到3-[[(4bS,8S,8aR)-4b,8-dimethyl-8-phenylmethoxycarbonyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl]oxy]propanoic acid
  参考文献：
  名称：

  Phenolic Diterpenoid Derivatives as Anti-Influenza A Virus Agents

  摘要：

  A series of diterpenoid derivatives based on podocarpic acid were synthesized and evaluated as anti influenza A virus agents. Several of the novel podocarpic acid derivatives exhibited nanomolar activities against an HINI influenza A virus (A/Puerto Rico/8/34) that was resistant to two anti-influenza drugs, oseltamivir and amantadine. This class of compounds inhibits the influenza virus by targeting the viral hemagglutinin-mediated membrane fusion. These results indicated that podocarpic acid derivatives may serve as potential drug candidates to fight drug-resistant influenza A virus infections.

  DOI：

  10.1021/ml500533x
• 作为产物：
  描述：

  罗汉松酸 、 1-benzylidene-2-(tert-butyldimethylsilyl)hydrazine 在 2-氯吡啶 、 亚碘酰苯 、 氢氟酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 11.5h， 以0.0273 g的产率得到podocarpic acid benzyl ester
  参考文献：
  名称：

  用（二氟碘）苯氧化 N-叔丁基二甲基甲硅烷基腙原位生成的重氮烷烃酯化羧酸的一般程序

  摘要：

  羧酸与重氮烷烃形成酯的双分子反应是最温和和最有效的有机转化之一，但除了重要的甲基酯化反应外，很少用于合成。这在很大程度上是由于作为底物的高级重氮烷烃难以接近且稳定性差的结果。在这项工作中，我们描述了一种通过用（二氟碘）苯氧化 N-叔丁基二甲基甲硅烷基腙 (TBSH) 来合成重氮烷烃的新方法，这是一种迄今为止未在腙氧化的背景下探索的试剂。当在羧酸底物存在下进行时，氧化导致有效的原位酯化。除了大大扩展了现在可用于酯化的重氮烷烃的范围之外，

  DOI：

  10.1021/ja0459779

文献信息

• Discovery and development of dimeric podocarpic acid leads as potent agonists of liver X receptor with HDL cholesterol raising activity in mice and hamsters
  作者：Sheo B. Singh、John G. Ondeyka、Weiguo Liu、Steve Chen、Tom S. Chen、Xiaohua Li、Aileen Bouffard、James Dropinski、A. Brian Jones、Sherrie McCormick、Nancy Hayes、Jianhua Wang、Neelam Sharma、Karen MacNaul、Melba Hernandez、Yu-Sheng Chao、Joanne Baffic、My-Hanh Lam、Charlotte Burton、Carl P. Sparrow、John G. Menke

  DOI：10.1016/j.bmcl.2005.03.100

  日期：2005.6

  identified podocarpic acid anhydride as a 1nM agonist of LXRalpha and beta receptors. Functionally this agonist was over 8-10-fold better activator of LXR receptors compared to one of the natural ligands, 22-(R)-hydroxy cholesterol, in HEK-293 cells. An imide analog increased the level of HDL by 26%, decreased LDL by 10.6%, and increased triglyceride by 51% in hamsters. Discovery, synthesis, SAR and

  肝X受体是调节胆固醇代谢的核受体。它们被氧固醇激活，导致ABCA1基因转录增加，促进胆固醇外流和HDL形成。我们已经确定了罗汉果酸酐为LXRalpha和β受体的1nM激动剂。在功能上，与HEK-293细胞中的天然配体之一22-（R）-羟基胆固醇相比，该激动剂的LXR受体活化剂高8-10倍。酰亚胺类似物使仓鼠的HDL水平提高了26％，LDL降低了10.6％，甘油三酸酯提高了51％。已经描述了发现，合成，SAR和二聚体活性的细节。
• Phenolic Diterpenoid Derivatives as Anti-Influenza A Virus Agents
  作者：Zhao Dang、Katherine Jung、Lei Zhu、Hua Xie、Kuo-Hsiung Lee、Chin-Ho Chen、Li Huang

  DOI：10.1021/ml500533x

  日期：2015.3.12

  A series of diterpenoid derivatives based on podocarpic acid were synthesized and evaluated as anti influenza A virus agents. Several of the novel podocarpic acid derivatives exhibited nanomolar activities against an HINI influenza A virus (A/Puerto Rico/8/34) that was resistant to two anti-influenza drugs, oseltamivir and amantadine. This class of compounds inhibits the influenza virus by targeting the viral hemagglutinin-mediated membrane fusion. These results indicated that podocarpic acid derivatives may serve as potential drug candidates to fight drug-resistant influenza A virus infections.
• A General Procedure for the Esterification of Carboxylic Acids with Diazoalkanes Generated in Situ by the Oxidation of <i>N</i>-<i>tert</i>-Butyldimethylsilylhydrazones with (Difluoroiodo)benzene
  作者：Michael E. Furrow、Andrew G. Myers

  DOI：10.1021/ja0459779

  日期：2004.10.1

  bimolecular reaction of carboxylic acids with diazoalkanes to form esters is among the mildest and most efficient of organic transformations but is seldom used in synthesis beyond the important case of methyl esterification. This is largely a consequence of the inaccessibility and poor stability of higher diazoalkanes as substrates. In this work we describe a new method for the synthesis of diazoalkanes by

  羧酸与重氮烷烃形成酯的双分子反应是最温和和最有效的有机转化之一，但除了重要的甲基酯化反应外，很少用于合成。这在很大程度上是由于作为底物的高级重氮烷烃难以接近且稳定性差的结果。在这项工作中，我们描述了一种通过用（二氟碘）苯氧化 N-叔丁基二甲基甲硅烷基腙 (TBSH) 来合成重氮烷烃的新方法，这是一种迄今为止未在腙氧化的背景下探索的试剂。当在羧酸底物存在下进行时，氧化导致有效的原位酯化。除了大大扩展了现在可用于酯化的重氮烷烃的范围之外，