squamostolide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: squamostolide
• 英文别名: (2S)-4-[(13R)-13-hydroxy-13-[(2R)-5-oxooxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• 化学式: C₂₂H₃₆O₅
• 分子量: 380.525
• InChiKey: RSLZRPNJKAWWIP-DFQSSKMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甘露醇 在 palladium on activated charcoal 吡啶 、 乙酰溴 、 氢气 、 乙酸酐 、 四丁基碘化铵 、 二正丁基氧化锡 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 20.0~110.0 ℃ 、101.33 kPa 条件下， 反应 47.17h， 生成 squamostolide
  参考文献：
  名称：

  Convergent total synthesis of squamostolide

  摘要：

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.151

文献信息

• Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I
  作者：Hidefumi Makabe、Yuka Kimura、Masaharu Higuchi、Hiroyuki Konno、Masatoshi Murai、Hideto Miyoshi

  DOI：10.1016/j.bmc.2005.12.015

  日期：2006.5

  A convergent stereoselective synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin and squamostolide was accomplished via a Pd-catalyzed cross-coupling reaction. The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed a remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin

  （4R，15R，16R，21S）-和（4R，15S，16S，21S）-rollicosin和方莫司肽的聚合立体选择性合成是通过Pd催化的交叉偶联反应完成的。用牛心脏线粒体NADH-泛醌氧化还原酶检查了这些化合物的抑制活性。与普通的醋酸原素（如布勒他汀）相比，这些化合物的抑制活性非常弱。我们的结果表明，要保持有效的抑制作用，羟基化内酯不能代替普通产乙酸原素中具有长烷基链的羟基化单或双THF环。
• Design, syntheses, and biological evaluations of squamostolide and its related analogs
  作者：Cheng-Lin Lee、Chi-Fong Lin、Wan-Ru Lin、Kun-Sheng Wang、Ya-her Chang、Shinne-Ren Lin、Yang-Chang Wu、Ming-Jung Wu

  DOI：10.1016/j.bmc.2005.05.050

  日期：2005.10

  Squamostolide and its related analogs were designed and synthesized for biological evaluation. All these compounds were tested for growth inhibition activities against human tumor cell lines, in which one of the compounds showed the most potent cyto-toxicity among these derivatives against a full panel of 60 human cancer cell lines. The same compound also showed G2/M phase arrest and a weak apoptotic effect during flow cytometric analysis. (c) 2005 Elsevier Ltd. All rights reserved.
• Convergent total synthesis of squamostolide
  作者：Kevin J. Quinn、Austin G. Smith、Carolyn M. Cammarano

  DOI：10.1016/j.tet.2007.03.151

  日期：2007.6

  A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from D-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished. (c) 2007 Elsevier Ltd. All rights reserved.