(5S,8S,9R)-8-benzoyl-2-[(E,1S,2S)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione | 1145685-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,8S,9R)-8-benzoyl-2-[(E,1S,2S)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
• CAS: 1145685-14-8
• 化学式: C₂₂H₂₅NO₈
• 分子量: 431.442
• InChiKey: SLYDIPAXCVVRNY-VXBYYLFASA-N

物化性质

• 沸点：
  751.5±60.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  反-3-已烯 、 伪神经素A 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(5S,8S,9R)-8-benzoyl-2-[(E,1S,2S)-1,2-dihydroxyhex-3-enyl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
  参考文献：
  名称：

  Pseurotin A and its analogues as inhibitors of immunoglobuline E production

  摘要：

  A natural product, pseurotin A inhibits IgE production in vitro. Wide variety of chemical modi. cation of pseurotin A was performed. Structure-activity relationship studies of pseurotin analogues elucidated that 10-deoxypseurotin A strongly inhibits IgE production with IC(50) of 0.066 mu M. An immunosuppressive activity of another natural product, synerazol was also found. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.029

文献信息

• Elucidation of Pseurotin Biosynthetic Pathway Points to Trans-Acting<i>C-</i>Methyltransferase: Generation of Chemical Diversity
  作者：Yuta Tsunematsu、Manami Fukutomi、Takayoshi Saruwatari、Hiroshi Noguchi、Kinya Hotta、Yi Tang、Kenji Watanabe

  DOI：10.1002/anie.201404804

  日期：2014.8.4

  Pseurotins comprise a family of structurally related Aspergillal natural products having interesting bioactivity. However, little is known about the biosynthetic steps involved in the formation of their complex chemical features. Systematic deletion of the pseurotin biosynthetic genes in A. fumigatus and in vivo and in vitro characterization of the tailoring enzymes to determine the biosynthetic intermediates

  Pseurotins 包括一系列结构相关的曲霉属天然产物，具有有趣的生物活性。然而，对其复杂化学特征的形成所涉及的生物合成步骤知之甚少。烟曲霉中假素生物合成基因的系统缺失描述了用于确定生物合成中间体的定制酶的体内和体外表征，以及负责形成每个中间体的基因产物。因此，阐明了导致从主要前体氮杂紫杉醇形成假素 A 的主要生物合成步骤。该研究揭示了假素家族化合物和中间体的生物合成的组合性质。最有趣的是，我们首次发现了环氧化酶C-甲基转移酶双功能融合蛋白 PsoF，它似乎可以反式甲基化新生的聚酮化合物骨架碳原子。
• Pseurotin A and its analogues as inhibitors of immunoglobuline E production
  作者：Minoru Ishikawa、Tomohisa Ninomiya、Hirotomo Akabane、Nobuaki Kushida、Go Tsujiuchi、Makoto Ohyama、Shuichi Gomi、Keiko Shito、Takashi Murata

  DOI：10.1016/j.bmcl.2009.01.029

  日期：2009.3

  A natural product, pseurotin A inhibits IgE production in vitro. Wide variety of chemical modi. cation of pseurotin A was performed. Structure-activity relationship studies of pseurotin analogues elucidated that 10-deoxypseurotin A strongly inhibits IgE production with IC(50) of 0.066 mu M. An immunosuppressive activity of another natural product, synerazol was also found. (C) 2009 Elsevier Ltd. All rights reserved.