(20S,22R)-5α-chloro-19,27-diacetyloxy-6β-hydroxy-1-oxowitha-2,24-dienolide

• 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: (20S,22R)-5α-chloro-19,27-diacetyloxy-6β-hydroxy-1-oxowitha-2,24-dienolide
• 英文别名: jaborosalactone E 19,27-diacetate；[(2R)-2-[(1S)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-10-(acetyloxymethyl)-5-chloro-6-hydroxy-13-methyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4-methyl-6-oxo-2,3-dihydropyran-5-yl]methyl acetate
• 化学式: C₃₂H₄₃ClO₈
• 分子量: 591.142
• InChiKey: AITVSJMNJIXYNH-CNWOLZSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  withalongolide A 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 甲酸铵 、 palladium diacetate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (20S,22R)-5α-chloro-19,27-diacetyloxy-6β-hydroxy-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

• 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.