Pseudopterolide | 83560-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: Pseudopterolide
• 英文别名: methyl (2S,4R,5R,11R,12R)-14-oxo-5,11-bis(prop-1-en-2-yl)-3,13,16-trioxatetracyclo[10.2.1.17,10.02,4]hexadeca-1(15),7,9-triene-8-carboxylate
• CAS: 83560-98-9
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: HGJODUIUVPXWLZ-ZMKKGPNFSA-N

物化性质

• 沸点：
  575.5±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Pseudopterolide 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (2R,3S,8S,9R,15R,Z)-8-hydroxy-12-(methoxycarbonyl)-N,N,N-trimethyl-5-oxo-2,9-di(prop-1-en-2-yl)-4,14-dioxatricyclo[9.2.1.13,6]pentadeca-1(13),6,11-trien-15-aminium iodide
  参考文献：
  名称：

  Furanocembranolide interconversions. Transformation of pseudopterolide into tobagolide and its reversal

  摘要：

  DOI：

  10.1016/s0040-4039(00)97102-8
• 作为产物：
  描述：

  (2R,3S,8S,9R,15R,Z)-8-hydroxy-12-(methoxycarbonyl)-N,N,N-trimethyl-5-oxo-2,9-di(prop-1-en-2-yl)-4,14-dioxatricyclo[9.2.1.13,6]pentadeca-1(13),6,11-trien-15-aminium iodide 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.33h， 生成 Pseudopterolide
  参考文献：
  名称：

  Furanocembranolide interconversions. Transformation of pseudopterolide into tobagolide and its reversal

  摘要：

  DOI：

  10.1016/s0040-4039(00)97102-8

文献信息

• Thiophilic reactions of pseudopterolide: Potential implications for its biological activity
  作者：Sunaina Sharma、Thomas M. Mesic、Robin A. Martin (in part)

  DOI：10.1016/s0040-4020(01)85501-0

  日期：——

  variety of biological processes including cell division. We examined the ability of pseudopterolide to add to the sulfhydryl groups of a number of thiol-containing substances and found that it initially binds covalently to the sulfhydryl groups via an SN2′ addition of sulfur to the α,β-unsaturated lactone with concomitant opening of the epoxide. Subsequent addition of the sulfhydryl group to the exocyclic

  伪蝶呤是一种加工乙烯基环氧化物的海洋天然产物，已显示出抑制多种生物过程的作用，包括细胞分裂。我们研究了拟蝶ero内酯加到许多含硫醇物质的巯基上的能力，发现它最初是通过将S N 2′加到α，β-不饱和内酯上并伴随硫的S N 2'共价键合到巯基上的。环氧的开放。随后将巯基加到环外烯酮上，通过最初的迈克尔加成反应，接着是明显的分子内SN ′，形成1，2-加合物。消除。我们建议拟pt虫内酯的生物学作用可能是由于该化合物添加到生物活性分子的硫醇基团上引起的。
• Lipidyl Pseudopteranes A−F: Isolation, Biomimetic Synthesis, and PTP1B Inhibitory Activity of a New Class of Pseudopteranoids from the Gorgonian <i>Pseudopterogorgia acerosa</i>
  作者：Abhijeet S. Kate、Isabelle Aubry、Michel L. Tremblay、Russell G. Kerr

  DOI：10.1021/np800544b

  日期：2008.12.26

  Novel lipidyl pseudopteranoids, lipidyl pseudopteranes A-F (1-6), have been isolated from the soft coral Pseudopterogorgia acerosa collected from the Bahamas. Structure elucidation of the six new compounds was based on 1D and 2D NMR data and mass spectrometry, and a biomimetic synthesis of 1 from pseudopterolide (7) was used to help establish its absolute configuration. These structures represent the first report of a pseudopterane diterpene with a fatty acid moiety. Lipidyl pseudopteranes A and D exhibited modest yet selective inhibitory activity against protein tyrosine phosphatase 1B, a promising drug target.
• Isolation, Biomimetic Synthesis, and Cytotoxic Activity of Bis(pseudopterane) Amines
  作者：Abhijeet S. Kate、Jason K. Pearson、Balaji Ramanathan、Kelly Richard、Russell G. Kerr

  DOI：10.1021/np8008144

  日期：2009.7.24

  LC-MS/MS-based screening of the dichloromethane extract of the gorgonian coral Pseudopterogorgia acerosa led to the isolation of a novel bis(pseudopterane) amine (1). The structural assignment of 1 was achieved by 1D and 2D NMR and mass spectrometry analysis. A biomimetic synthesis of 1 and the known symmetrical diterpene 2 from pseudopterolide (3) is described in this report. Bis(pseudopterane) amine showed selective growth inhibition activity against cancer cell lines with IC50 values of 4.2 mu M (HCT116) and 42 mu M (HeLa).
• PAQUETTE, LEO A.;ASTLES, PETER C., TETRANEDRON LETT., 31,(1990) N5, C. 6505-6508
  作者：PAQUETTE, LEO A.、ASTLES, PETER C.

  DOI：——

  日期：——