iso-PsE | 1046779-95-6

• 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: iso-PsE
• 英文别名: (2S,3S,4R,5S,6S)-2-[[(4R,6S,6aR,9S)-2-hydroxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]oxy]-6-methyloxane-3,4,5-triol
• CAS: 1046779-95-6
• 化学式: C₂₆H₃₈O₆
• 分子量: 446.584
• InChiKey: KPQRZOMZOFKSLE-QBCISGOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  iso-PsE 、 4-甲氧基苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到(3aR,4S,6S,7S,7aS)-6-(((3S,7R,9S,9aR)-5-hydroxy-3,6,9-trimethyl-7-(2-methylprop-1-en-1-yl)-2,3,7,8,9,9a-hexahydro-1H-phenalen-4-yl)oxy)-2-(4-methoxyphenyl)-4-methyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol
  参考文献：
  名称：

  Exploration and determination of the redox properties of the pseudopterosin class of marine natural products

  摘要：

  We describe herein the redox chemistry of the pseudopterosin class of marine natural products. Known for their anti-inflammatory and wound healing properties, their chemistry has largely gone unexplored. Details of both voltammetric and preparative scale experiments are provided and speculation is provided concerning the potential role of electron transfer chemistry in the expression of pseudopterosin bioactivity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.021

文献信息

• Synthesis and an Evaluation of the Bioactivity of the <i>C</i>-Glycoside of Pseudopterosin A Methyl Ether
  作者：Wei Zhong、Claudia Moya、R. S. Jacobs、R. Daniel Little

  DOI：10.1021/jo801432t

  日期：2008.9.19

  The Suzuki-Miyaura cross-coupling protocol was applied to the synthesis of 1a, the C-glycoside analogue of PsA methyl ether. This marks the first construction of a C-glycoside for this class of marine natural products, thereby offering an opportunity to compare its bioactivity to the natural substances. Its activity profile resembled that of PsA (1) and PsA O-methyl ether (1b) when assayed for its anti-inflammatory activity and its ability to inhibit phagocytosis. We conclude that the intact structure is present when a pseudopterosin expresses its anti-inflammatory and phagocytosis inhibitory properties and that they are, therefore, not likely to be prodrugs. Results show that 1a is an effective binding agent toward the A(2A) and A(3) adenosine receptors, displaying IC50 values of 20 and 10 mu M, respectively.
• Exploration and determination of the redox properties of the pseudopterosin class of marine natural products
  作者：Wei Zhong、R. Daniel Little

  DOI：10.1016/j.tet.2009.09.021

  日期：2009.12

  We describe herein the redox chemistry of the pseudopterosin class of marine natural products. Known for their anti-inflammatory and wound healing properties, their chemistry has largely gone unexplored. Details of both voltammetric and preparative scale experiments are provided and speculation is provided concerning the potential role of electron transfer chemistry in the expression of pseudopterosin bioactivity. (c) 2009 Elsevier Ltd. All rights reserved.