(4S,20S,22R)-27-acetyloxy-4β,19-dihydroxy-5β,6β-epoxy-1-oxowitha-2,24-dienolide | 1391916-28-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (4S,20S,22R)-27-acetyloxy-4β,19-dihydroxy-5β,6β-epoxy-1-oxowitha-2,24-dienolide
• 英文别名: withalongolide A 27-acetate；[(2R)-2-[(1S)-1-[(1S,2S,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-2-(hydroxymethyl)-16-methyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-15-yl]ethyl]-4-methyl-6-oxo-2,3-dihydropyran-5-yl]methyl acetate
• CAS: 1391916-28-1
• 化学式: C₃₀H₄₀O₈
• 分子量: 528.643
• InChiKey: FZFILTXAMHYFLP-NSXHFEBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,20S,22R)-27-acetyloxy-4β,19-dihydroxy-5β,6β-epoxy-1-oxowitha-2,24-dienolide 、 4-戊烯酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.5h， 以92%的产率得到(4S,20S,22R)-27-acetyloxy-4β,19-di-pent-4-enoyloxy-5β,6β-epoxy-1-oxowitha-2,24-dienolide
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues

  摘要：

  The natural product withaferin A exhibits potent antitumor activity and other diverse pharmacological activities. The recently discovered withalongolide A, a C-19 hydroxylated congener of withaferin A, was recently reported to possess cytotoxic activity against head and neck squamous cell carcinomas. Semisynthetic acetylated analogues of withalongolide A were shown to be considerably more cytotoxic than the parent compound. To further explore the structure activity relationships, 20 new semisynthetic analogues of withalongolide A were synthesized and evaluated for cytotoxic activity against four different cancer cell lines. A number of derivatives were found to be more potent than the parent compound and withaferin A.

  DOI：

  10.1021/ml400267q
• 作为产物：
  描述：

  withalongolide A 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以25%的产率得到(4S,20S,22R)-27-acetyloxy-4β,19-dihydroxy-5β,6β-epoxy-1-oxowitha-2,24-dienolide
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues

  摘要：

  The natural product withaferin A exhibits potent antitumor activity and other diverse pharmacological activities. The recently discovered withalongolide A, a C-19 hydroxylated congener of withaferin A, was recently reported to possess cytotoxic activity against head and neck squamous cell carcinomas. Semisynthetic acetylated analogues of withalongolide A were shown to be considerably more cytotoxic than the parent compound. To further explore the structure activity relationships, 20 new semisynthetic analogues of withalongolide A were synthesized and evaluated for cytotoxic activity against four different cancer cell lines. A number of derivatives were found to be more potent than the parent compound and withaferin A.

  DOI：

  10.1021/ml400267q

文献信息

• Withanolide Isolated from Physalis longifolia and Analogs and Methods of Use Thereof
  申请人：Timmermann Barbara N.

  公开号：US20120196815A1

  公开（公告）日：2012-08-02

  The present invention features novel withanolides, as well as analogs and salts thereof, for use in the treatment of proliferative disease, cardiovascular disease, neurodegenerative disease and inflammatory disease.
• Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues
  作者：Hashim F. Motiwala、Joseph Bazzill、Abbas Samadi、Huaping Zhang、Barbara N. Timmermann、Mark S. Cohen、Jeffrey Aubé

  DOI：10.1021/ml400267q

  日期：2013.11.14

  The natural product withaferin A exhibits potent antitumor activity and other diverse pharmacological activities. The recently discovered withalongolide A, a C-19 hydroxylated congener of withaferin A, was recently reported to possess cytotoxic activity against head and neck squamous cell carcinomas. Semisynthetic acetylated analogues of withalongolide A were shown to be considerably more cytotoxic than the parent compound. To further explore the structure activity relationships, 20 new semisynthetic analogues of withalongolide A were synthesized and evaluated for cytotoxic activity against four different cancer cell lines. A number of derivatives were found to be more potent than the parent compound and withaferin A.