差向伊快霉素(差向尹奎色亭) | 255377-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 差向伊快霉素(差向尹奎色亭)
• 英文名称: 5'-epiequisetin
• 英文别名: equisetin；Epiequisetin；(3E,5R)-3-[[(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione
• CAS: 255377-45-8
• 化学式: C₂₂H₃₁NO₄
• 分子量: 373.492
• InChiKey: QNQBPPQLRODXET-YPFNAWONSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

表木贼素是一种次级代谢产物，具有抗菌活性。

反应信息

• 作为产物：
  描述：

  尹奎色亭 以 吡啶 为溶剂， 生成 差向伊快霉素(差向尹奎色亭)
  参考文献：
  名称：

  Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase

  摘要：

  Integration is an essential step in HN replication and is catalyzed by an enzyme called integrase. We have isolated equisetin (la), and a novel opposite stereochemical homolog, phomasetin (2a), from Fusarium heterosporum and a Phoma sp. respectively. They inhibit the invitro recombinant integrase enzyme with IC50 values of 7-20 mu M. Unlike known inhibitors, these compounds also inhibit the integration reactions catalyzed by preintegration complexes isolated from HIV-I infected cells. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00269-x

文献信息

• Enantioselective total synthesis of (−)-equisetin using a Me3Al-mediated intramolecular Diels–Alder reaction
  作者：Kumiko Yuki、Mitsuru Shindo、Kozo Shishido

  DOI：10.1016/s0040-4039(01)00217-9

  日期：2001.3

  An efficient and enantioselective total synthesis of (−)-equisetin 1 has been accomplished using a diastereoselective Me3Al-mediated intramolecular Diels–Alder (IMDA) reaction as a key reaction step.

  使用非对映选择性Me 3 Al介导的分子内Diels-Alder（IMDA）反应作为关键反应步骤，可以完成（-）-equisetin 1的高效和对映选择性合成。
• Characterization of the Fusarium toxin equisetin: the use of phenylboronates in structure assignment
  作者：N. J. Phillips、J. T. Goodwin、A. Fraiman、R. J. Cole、D. G. Lynn

  DOI：10.1021/ja00203a025

  日期：1989.10
• Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase
  作者：Sheo B. Singh、Deborah L. Zink、Michael A. Goetz、Anne W. Dombrowski、Jon D. Polishook、Daria J. Hazuda

  DOI：10.1016/s0040-4039(98)00269-x

  日期：1998.4

  Integration is an essential step in HN replication and is catalyzed by an enzyme called integrase. We have isolated equisetin (la), and a novel opposite stereochemical homolog, phomasetin (2a), from Fusarium heterosporum and a Phoma sp. respectively. They inhibit the invitro recombinant integrase enzyme with IC50 values of 7-20 mu M. Unlike known inhibitors, these compounds also inhibit the integration reactions catalyzed by preintegration complexes isolated from HIV-I infected cells. (C) 1998 Elsevier Science Ltd. All rights reserved.