(S)-3-((S)-13-hydroxy-13-((2S,5R)-5-((S)-1-hydroxytridecyl) tetrahydrofuran-2-yl)tridecyl)-5-methylfuran-2(5H)-one | 1017587-49-3

• 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: (S)-3-((S)-13-hydroxy-13-((2S,5R)-5-((S)-1-hydroxytridecyl) tetrahydrofuran-2-yl)tridecyl)-5-methylfuran-2(5H)-one
• 英文别名: squafosacin F；(2S)-4-[(13S)-13-hydroxy-13-[(2S,5R)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS: 1017587-49-3
• 化学式: C₃₅H₆₄O₅
• 分子量: 564.89
• InChiKey: RBSBTRALZZSVBA-OBLXJGCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  40
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-((S)-13-hydroxy-13-((2S,5R)-5-((S)-1-hydroxytridecyl) tetrahydrofuran-2-yl)tridecyl)-5-methylfuran-2(5H)-one 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 氘代吡啶 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Mono-tetrahydrofuran Annonaceous Acetogenins from Annona squamosa as Cytotoxic Agents and Calcium Ion Chelators

  摘要：

  Eight new mono-tetrahydrofuran (THF)-type annonaceous acetogenins, squafosacins B, C, F, and G (1-4), squadiolins A-C (5-7), and cis-annotemoyin-1 (8), as well as eight known annonaceous acetogenins, glabranin, annotemoyins-1 and -2, bullatencin, cis-bullatencin, and uvariamicins-I, -II, and -III, were isolated from the seeds of Annona squamosa by HPLC. The structures of all new isolates were elucidated by using spectroscopic and chemical methods. Squadiolins A (5) and B (6) showed ng/mL potency against human Hep G2 hepatoma cells and significant cytotoxic activity against human MDA-MB-231 breast cancer cells. Squafosacin B (1) also exhibited significant cytotoxic activity against human Hep G2 and 313 hepatoma and MCF-7 breast cancer cells. In addition, the chelation of mono-THF acetogenins with calcium ions was investigated using isothermal titration calorimetry.

  DOI：

  10.1021/np0704957
• 作为产物：
  描述：

  trans,trans-2,6-octadiene-1,8-diol 在 吡啶 、 titanium(IV) isopropylate 、 甲醇 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 copper(l) iodide 、 正丁基锂 、 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 、 二甲基硫 、 5%-palladium/activated carbon 、 Rh/Al₂O₃ 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 四丁基氟化铵 、 水 、 氢气 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 、 D-(-)-酒石酸二异丙酯 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.5h， 生成 (S)-3-((S)-13-hydroxy-13-((2S,5R)-5-((S)-1-hydroxytridecyl) tetrahydrofuran-2-yl)tridecyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  squafosacin F 的全合成：单四氢呋喃 acetogenins 的立体发散方法†

  摘要：

  番荔枝素具有广泛的潜在生物活性。因此，开发简单且面向多样性的合成方法非常重要。我们已经实现了 squafosacin F 的首次全合成并确定了它的绝对构型。关键步骤是酸介导的串联分子内双环化，以构建羟基侧翼的单四氢呋喃核心，并通过高度立体选择性反应以目标天然产物的所需功能进行装饰。

  DOI：

  10.1039/c9ra09762g

文献信息

• Total synthesis of squafosacin F: stereodivergent approach to mono-tetrahydrofuran acetogenins
  作者：Koichiro Ota、Sumika Kohno、Tomoko Yamashita、Atsuko Miura、Kazuo Kamaike、Hiroaki Miyaoka

  DOI：10.1039/c9ra09762g

  日期：——

  to their synthesis is therefore important. We have achieved the first total synthesis of squafosacin F and assigned its absolute configuration. The key steps were an acid-mediated tandem intramolecular double cyclization to build the hydroxy-flanked mono-tetrahydrofuran core and decoration with the desired functionalities of the target natural product via highly stereoselective reactions.

  番荔枝素具有广泛的潜在生物活性。因此，开发简单且面向多样性的合成方法非常重要。我们已经实现了 squafosacin F 的首次全合成并确定了它的绝对构型。关键步骤是酸介导的串联分子内双环化，以构建羟基侧翼的单四氢呋喃核心，并通过高度立体选择性反应以目标天然产物的所需功能进行装饰。
• Mono-tetrahydrofuran Annonaceous Acetogenins from <i>Annona squamosa</i> as Cytotoxic Agents and Calcium Ion Chelators
  作者：Chih-Chuang Liaw、Yu-Liang Yang、Mei Chen、Fang-Rong Chang、Shu-Li Chen、Shih-Hsiung Wu、Yang-Chang Wu

  DOI：10.1021/np0704957

  日期：2008.5.1

  Eight new mono-tetrahydrofuran (THF)-type annonaceous acetogenins, squafosacins B, C, F, and G (1-4), squadiolins A-C (5-7), and cis-annotemoyin-1 (8), as well as eight known annonaceous acetogenins, glabranin, annotemoyins-1 and -2, bullatencin, cis-bullatencin, and uvariamicins-I, -II, and -III, were isolated from the seeds of Annona squamosa by HPLC. The structures of all new isolates were elucidated by using spectroscopic and chemical methods. Squadiolins A (5) and B (6) showed ng/mL potency against human Hep G2 hepatoma cells and significant cytotoxic activity against human MDA-MB-231 breast cancer cells. Squafosacin B (1) also exhibited significant cytotoxic activity against human Hep G2 and 313 hepatoma and MCF-7 breast cancer cells. In addition, the chelation of mono-THF acetogenins with calcium ions was investigated using isothermal titration calorimetry.