(5S)-3-[8-hydroxy-12-[2-(2-undec-2-ynoxyethoxy)ethoxy]dodec-10-ynyl]-4-(methoxymethoxy)-5-methyloxolan-2-one | 286471-03-2

• 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)-3-[8-hydroxy-12-[2-(2-undec-2-ynoxyethoxy)ethoxy]dodec-10-ynyl]-4-(methoxymethoxy)-5-methyloxolan-2-one
• CAS: 286471-03-2
• 化学式: C₃₄H₅₈O₈
• 分子量: 594.83
• InChiKey: DFOWZPLEVZLODT-IMDVACINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  42
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5S)-3-[8-hydroxy-12-[2-(2-undec-2-ynoxyethoxy)ethoxy]dodec-10-ynyl]-4-(methoxymethoxy)-5-methyloxolan-2-one 在 platinum(IV) oxide 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 (2S)-4-[8-hydroxy-12-[2-(2-undecoxyethoxy)ethoxy]dodecyl]-2-methyl-2H-furan-5-one
  参考文献：
  名称：

  Polyether Mimics of Naturally Occurring Cytotoxic Annonaceous Acetogenins

  摘要：

  On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.

  DOI：

  10.1021/jm990575a
• 作为产物：
  描述：

  二乙二醇双(2-丙炔基)醚 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 9.75h， 生成 (5S)-3-[8-hydroxy-12-[2-(2-undec-2-ynoxyethoxy)ethoxy]dodec-10-ynyl]-4-(methoxymethoxy)-5-methyloxolan-2-one
  参考文献：
  名称：

  Polyether Mimics of Naturally Occurring Cytotoxic Annonaceous Acetogenins

  摘要：

  On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.

  DOI：

  10.1021/jm990575a

文献信息

• Polyether Mimics of Naturally Occurring Cytotoxic Annonaceous Acetogenins
  作者：Zhu-Jun Yao、Hai-Ping Wu、Yu-Lin Wu

  DOI：10.1021/jm990575a

  日期：2000.6.1

  On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.