taccalonolide AM | 1415799-75-5

• 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: taccalonolide AM
• 英文别名: [(1S,2R,3R,5R,7S,9S,10R,11S,12S,14S,15R,16S,17S,22S,23S,24R,25R)-14-acetyloxy-3,5,22,25-tetrahydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-10-yl] 3-methylbutanoate
• CAS: 1415799-75-5
• 化学式: C₃₅H₄₈O₁₂
• 分子量: 660.759
• InChiKey: ZNLKACXIVDJYHF-ZSYXIPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  taccalonolide E 在 水 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 taccalonolide AK 、 taccalonolide AL 、 taccalonolide AM 、 taccalonolide AN 、 taccalonolide N
  参考文献：
  名称：

  Hydrolysis Reactions of the Taccalonolides Reveal Structure–Activity Relationships

  摘要：

  The taccalonolides are microtubule stabilizers isolated from plants of the genus Tacca that show potent in vivo antitumor activity and the ability to overcome multiple mechanisms of drug resistance. The most potent taccalonolide identified to date, AJ, is a semisynthetic product generated from the major plant metabolite taccalonolide A in a two-step reaction. The first step involves hydrolysis of taccalonolide A to generate taccalonolide B, and then this product is oxidized to generate an epoxide group at C-22-C-23. To generate sufficient taccalonolide AJ for in vivo antitumor efficacy studies, the hydrolysis conditions for the conversion of taccalonolide A to B were optimized. During purification of the hydrolysis products, we identified the new taccalonolide AO (1) along with taccalonolide I. When the same hydrolysis reaction was performed on a taccalonolide E-enriched fraction, four new taccalonolides, assigned as AK, AL, AM, and AN (2-5), were obtained in addition to the expected product taccalonolide N. Biological assays were performed on each of the purified taccalonolides, which allowed for increased refinement of the structure-activity relationship of this class of compounds.

  DOI：

  10.1021/np400435t