ecdysone 2,3,22-triacetate | 19466-43-4

• 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: ecdysone 2,3,22-triacetate
• 英文别名: [(2S,3R,5R,9R,10R,13R,14S,17R)-2-acetyloxy-17-[(2S,3R)-3-acetyloxy-6-hydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 19466-43-4
• 化学式: C₃₃H₅₀O₉
• 分子量: 590.755
• InChiKey: NNVBLQDIPNCOCY-HSCIAUBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ecdysone 2,3,22-triacetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 蜕皮激素
  参考文献：
  名称：

  Nakano, Kimiko; Murakami, Kotaro; Nohara, Toshihiro, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 5, p. 1445 - 1451

  摘要：

  DOI：
• 作为产物：
  描述：

  蜕皮激素 、 乙酸酐 在 吡啶 作用下， 以88%的产率得到ecdysone 2,3,22-triacetate
  参考文献：
  名称：

  Ecdysteroid Derivatives that Reverse P-Glycoprotein-Mediated Drug Resistance

  摘要：

  The expression of multidrug resistance P-glycoprotein (P-gp) by cancer cells represents one of the major drawbacks to successful cancer therapy. Accordingly, the development of drugs that inhibit the activity of this transporter remains a major challenge in cancer drug discovery. In this context, several new ecdysteroid derivatives have been synthesized and evaluated as P-gp inhibitors. Two of them (compounds 9 and 14) were able to resensitize CEMVbl100 and LoVo(Doxo) resistant cell lines to vinblastine and doxorubicin, respectively. Indeed, both compounds 9 and 14 increased the cellular accumulation of rhodamine 123 in cells expressing P-gp and stimulated basal P-glycoprotein-ATPase activity at a 1 mu M concentration, demonstrating their interference with the transport of other substrates in a competitive mode. Moreover, in a medulloblastoma cell line (DAOY), compounds 9 and 14 reduced the side population representing cancer stem cells, which are characterized by a high expression of ABC drug transporters. Further, in DAOY cells, the same two compounds synergized with cisplatin and vincristine, two drugs used commonly in the therapy of medulloblastoma. Molecular docking studies on the homology-modeled structure of the human P-glycoprotein provided a rationale for the biological results, validating the binding mode within the receptor site, in accordance with lipophilicity data and observed structure-activity relationship information. Altogether, the present results endorse these derivatives as promising P-gp inhibitors, and they may serve as candidates to reverse drug resistance in cancer cells.

  DOI：

  10.1021/acs.jnatprod.0c00334

文献信息

• A convenient synthesis of 25-deoxyecdysone, a major secretory product of crustacean Y-organs and of 2,25-dideoxyecdysone, its putative immediate precursor
  作者：Jaroslav Pis、Jean-Pierre Girault、Marc Larchevêque、Chantal Dauphin-Villemant、René Lafont

  DOI：10.1016/0039-128x(94)00035-b

  日期：1995.2

  25-Deoxyecdysone, a major secretory product of Y-organs of at least several species of crustaceans and the immediate precursor of circulating ponasterone A in these animals, can easily be synthesized from ecdysone. The present four-step procedure involves the formation of a mixture of Delta(24,25) and Delta(25,26) intermediates which might also be used to prepare a labeled reference compound for metabolic or binding studies. Similarly, 2,25-dideoxyecdysone was prepared from 2-deoxyecdysone. These compounds have been used to identify metabolites of [H-3]-2,22,25-trideoxyecdysone (=5 beta-ketodiol) formed by Y-organs of the shore crab, Carcinus maenas.