Australifunginol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Australifunginol
• 英文别名: (4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-(3-hydroxypropanoyl)-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1-one
• 化学式: C₂₃H₃₈O₆
• 分子量: 410.551
• InChiKey: SIPMDGHVOPMZQY-VLBDLMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Australifungin 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Australifunginol
  参考文献：
  名称：

  Structure Elucidation of Australifungin, a Potent Inhibitor of Sphinganine N-Acyltransferase in Sphingolipid Biosynthesis from Sporormiella australis

  摘要：

  The structure elucidation of the novel, potent sphinganine N-acyltransferase inhibitor, australifungin (1), from Sporormiella australis is described. Extensive exchange-broadening phenomena predominantly of the keto-enol type were observed on the NMR time scale which was resolved by derivatization to triacetate (2) and tetraacetate (3) derivatives. Residual exchange broadening in the acetates was attributed to hindered rotation about the C3-C11 single bond which was frozen out into two conformers at low temperature, The application of 2D NMR techniques to the structure elucidation of the acetate derivatives at ambient and low temperature therefore contributed considerably to the overall structure determination of 1. The conformation and complete relative stereochemistry followed from a consideration of the Karplus relationship for H-1-H-1 vicinal coupling constants and phase-sensitive NOE data. Temperature-dependent NMR experiments suggest an averaged conformational mixture of four to five forms in solution at ambient temperature whereas a predominant conformer 1 is indicated at low temperature with the enolized beta-keto aldehyde stabilized through internal H-bonding in the cis-orientation. The triacetate 2 and tetraacetate 3, by contrast, are enolized in the sterically favored trans configuration. The beta-keto alcohol derivative australifunginol (6) is also present.

  DOI：

  10.1021/jo00111a040

文献信息

• Phosphonate analogs of HIV integrase inhibitor compounds
  申请人：Cai R. Zhenhong

  公开号：US20060116356A1

  公开（公告）日：2006-06-01

  Novel HIV integrase inhibitor compounds having at least one phosphonate group, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.

  本发明揭示了至少具有一个膦酸酯基团的新型HIV整合酶抑制剂化合物，其保护中间体以及用于抑制HIV整合酶的方法。
• Phosphonate Analogs Of Hiv Integrase Inhibitor Compounds
  申请人：Cai R. Zhenhong

  公开号：US20080076738A1

  公开（公告）日：2008-03-27

  Novel HIV integrase inhibitor compounds having at least one phosphonate group, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.

  本发明公开了至少具有一个膦酸酯基团的新型HIV整合酶抑制剂化合物、其受保护的中间体以及用于抑制HIV整合酶的方法。
• HIV integrase inhibitors
  申请人：——

  公开号：US20020045658A1

  公开（公告）日：2002-04-18

  Compounds useful in the inhibition of HIV integrase, the prevention or treatment of infection by HV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines are described. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. The culture Cytospora sp. MF 6608 (ATCC PTA-1691) is also disclosed, as well as processes for making a compound of the present invention employing the culture.

  本文描述了可用于抑制 HIV 整合酶、预防或治疗 HV 感染以及治疗艾滋病的化合物，这些化合物可以是化合物、药学上可接受的盐、药物组合成分，也可以是与其他抗病毒药物、免疫调节剂、抗生素或疫苗的组合。还描述了治疗艾滋病的方法和预防或治疗艾滋病毒感染的方法。还公开了细胞孢子培养物 MF 6608（ATCC PTA-1691），以及利用该培养物制造本发明化合物的工艺。
• PHOSPHONATE ANALOGS OF HIV INTEGRASE INHIBITOR COMPOUNDS
  申请人：GILEAD SCIENCES, INC.

  公开号：EP1742642A2

  公开（公告）日：2007-01-17
• US6541515B2
  申请人：——

  公开号：US6541515B2

  公开（公告）日：2003-04-01