(5S)-5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]furan-2(5H)-one | 206131-77-3

• 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: (5S)-5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]furan-2(5H)-one
• 英文别名: (S)-5-methyl-3-((13Z,17Z)-triaconta-13,17-dien-1-yl)furan-2(5H)-one；(+)-muricadienin；muricadienin；(5S)-5-Methyl-3-(13Z,17Z)-13,17-triacontadien-1-yl-2(5H)-furanone；(2S)-2-methyl-4-[(13Z,17Z)-triaconta-13,17-dienyl]-2H-furan-5-one
• CAS: 206131-77-3
• 化学式: C₃₅H₆₂O₂
• 分子量: 514.876
• InChiKey: ZZXWNKPYSIVFNM-YZKHSXCESA-N

物化性质

• 沸点：
  609.6±24.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  37
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (S)-2-acetyloxypropanoate 在 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三正丁基氢锡 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (5S)-5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]furan-2(5H)-one
  参考文献：
  名称：

  Short Route to the Total Synthesis of Natural Muricadienin and Investigation of Its Cytotoxic Properties

  摘要：

  An original synthesis of the acetogenin muricadienin, the bioprecursor of solamin, has been developed. The key step in the five-step 41% overall yield synthesis is the catalytic cross-cydomagnesiation reaction of functionally substituted 1,2-dienes with EtMgBr in the presence of Cp2TiCl2 and magnesium metal. It has been demonstrated for the first time that muricadienin exhibits a moderate in vitro inhibitory activity against topoisomerases I and II alpha, key cell cycle enzymes. Using flow cytometry, muricadienin was shown to have high cytotoxicity toward the HEK293 kidney cancer cells (IC50 0.39 mu M).

  DOI：

  10.1021/acs.jnatprod.6b00335

文献信息

• Total Synthesis of Muricadienin, the Putative Key Precursor in the Solamin Biosynthesis
  作者：Juliane Adrian、Christian B. W. Stark

  DOI：10.1021/ol502849y

  日期：2014.11.21

  The first total synthesis of muricadienin, the unsaturated putative precursor in the biosynthesis of trans- and cis-solamin is described. Key steps in the synthesis are a chemoselective hydroboration, a Z-selective Wittig reaction, and a Fries rearrangement for introducing the terminal α-substituted butenolide. Thus, muricadienin can be synthesized in 11 steps from commercially available starting materials

  muricadienin的第一全合成，在生物合成的不饱和前体的推定反式-和顺-solamin进行说明。合成的关键步骤是化学选择性硼氢化反应，Z选择性维蒂希反应和用于引入末端α-取代的丁烯内酯的弗里斯重排。因此，可以从市售起始原料中以11个步骤合成穆拉卡迪宁，总产率为42％。
• Short Route to the Total Synthesis of Natural Muricadienin and Investigation of Its Cytotoxic Properties
  作者：Usein M. Dzhemilev、Vladimir A. D’yakonov、Regina A. Tuktarova、Lilya U. Dzhemileva、Svetlana R. Ishmukhametova、Milyausha M. Yunusbaeva、Armin de Meijere

  DOI：10.1021/acs.jnatprod.6b00335

  日期：2016.8.26

  An original synthesis of the acetogenin muricadienin, the bioprecursor of solamin, has been developed. The key step in the five-step 41% overall yield synthesis is the catalytic cross-cydomagnesiation reaction of functionally substituted 1,2-dienes with EtMgBr in the presence of Cp2TiCl2 and magnesium metal. It has been demonstrated for the first time that muricadienin exhibits a moderate in vitro inhibitory activity against topoisomerases I and II alpha, key cell cycle enzymes. Using flow cytometry, muricadienin was shown to have high cytotoxicity toward the HEK293 kidney cancer cells (IC50 0.39 mu M).