[(3R,4E,16E,18R)-18-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyicosa-4,16-dien-1,19-diyn-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1446512-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3R,4E,16E,18R)-18-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyicosa-4,16-dien-1,19-diyn-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1446512-49-7
• 化学式: C₄₀H₄₄F₆O₆
• 分子量: 734.776
• InChiKey: YJIJNVDCZZPVTL-QCWSAMOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  52
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (+)-(3S,4E,16E,18S)-icosa-4,16-diene-1,19-diyne-3,18-diol 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以1.1 mg的产率得到[(3R,4E,16E,18R)-18-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyicosa-4,16-dien-1,19-diyn-3-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp.

  摘要：

  An optically inactive C-20 bisacetylenic alcohol, (4E,16E)-icosa-4,16-diene-1,19-diyne-3,18-diol, was isolated from a marine sponge Callyspongia sp. as a result of screening of antilymphangiogenic agents from marine invertebrates. An optical resolution using chiral-phase HPLC gave each enantiomer, (-)-1 and (+)-2. Because the natural and synthetic enantiomers 1 and 2 showed different biological properties, we investigated the structure activity relationships of bisacetylenic alcohols using 11 synthetic derivatives, and it is clarified that the essential structural unit for antiproliferative activity is the "1-yn-3-ol" on both termini and that there is a minimum chain length that connects the "1-yn-3-ol" moieties.

  DOI：

  10.1021/np400297p