2-deoxy-α-ecdysone 3,22-diacetate

• 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: 2-deoxy-α-ecdysone 3,22-diacetate
• 英文别名: 2-Deoxyecdysone 3,22-Diacetate；[(3S,5R,9R,10R,13R,14S,17R)-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
• 化学式: C₃₁H₄₈O₇
• 分子量: 532.718
• InChiKey: MESNNAYLENYFHI-SQTPKQKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-deoxy-α-ecdysone 3,22-diacetate 在 chromium(VI) oxide 、 氢氧化钾 、 水 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 30.67h， 生成 silenosterone
  参考文献：
  名称：

  Synthesis of silenosterone, an insect-molting hormone

  摘要：

  Silenosterone is synthesized in five steps: acetylation of 2-desoxy-alpha-ecdysone (1), saponification of 2-desoxy-alpha-ecdysone-3,22-diacetate (2) to the 22-monoacetate (3), and oxidation of the latter to a ketone (4) and its base hydrolysis (5). The structures of the compounds are confirmed by PMR, IR spectroscopy, and mass spectrometry.

  DOI：

  10.1007/bf02236295
• 作为产物：
  描述：

  乙酸酐 、 (3S,5R,9R,10R,13R,17R)-17-[(2S,3R)-3,6-二羟基-6-甲基庚烷-2-基]-3,14-二羟基-10,13-二甲基-2,3,4,5,9,11,12,15,16,17-十氢-1H-环戊二烯并[a]菲-6-酮 在 吡啶 作用下， 以3.2 mg的产率得到2-deoxy-α-ecdysone 3,22-diacetate
  参考文献：
  名称：

  来自石竹 L. 的植物蜕皮类固醇：结构和抗神经炎症评估

  摘要：

  六种未描述的 C 27 -植物蜕皮甾体衍生物，命名为超蜕皮激素 A-F，和十种已知的类似物是从石竹全株中提取的。它们的结构通过广泛的光谱学、质谱法、化学转化、手性 HPLC 分析和单晶X射线衍射分析。超蜕皮激素 A 和 B 在侧链上有一个四氢呋喃环，而超蜕皮激素 C-E 是罕见的植物蜕皮激素，含有 ( R)-乳酸部分，而超蜕皮激素 F 是一种不常见的 B 环修饰蜕皮激素。值得注意的是，基于超蜕皮激素 C 的可变温度（从 333 K 到 253 K）NMR 实验，缺失的碳信号在 253 K 处可见并已分配。评估了所有化合物的神经炎症生物测定，22-acetyl-2-deoxyecdysone, 2-deoxy-20-hydroxyecdysone, 20-hydroxyecdysone, ecdysterone-22- O-benzoate, 20-hydroxyecdysone - 20,22-

  DOI：

  10.1016/j.phytochem.2023.113710

文献信息

• Phytoecdysteroids of plants of the genus Silene. XI. 2-Deoxy-α-ecdysone 3-acetate from Silene scabrifolia
  作者：Z. Saatov、M. B. Gorovich、N. K. Abubakirov

  DOI：10.1007/bf00579812

  日期：1986.7
• 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.
• Significant Activity of Ecdysteroids on the Resistance to Doxorubicin in Mammalian Cancer Cells Expressing the Human ABCB1 Transporter
  作者：Ana Martins、Noémi Tóth、Attila Ványolós、Zoltán Béni、István Zupkó、József Molnár、Mária Báthori、Attila Hunyadi

  DOI：10.1021/jm300424n

  日期：2012.6.14

  Multidrug resistance (MDR) is a major cause of failure of cancer chemotherapy. Fifty-eight ecdysteroids, herbal analogues of the insect molting hormone and their semisynthetic derivatives, were tested for their activity against L5178 mouse T-cell lymphoma cells (non-MDR) and their subcell line transfected with pHa MDR1/A retrovirus overexpressing the human ABCB1 efflux pump (MDR cell line). The compounds showed very low antiproliferative activities but modulated the efflux of rhodamine 123 mediated by the ABCB1 transporter. Roughly depending on the polarity, mild to strong synergism or antagonism was observed by combining ecdysteroids with doxorubicin, and specific structure-activity relationships were also found. Our results show the effect of ecdysteroids on MDR cancer cells for the first time. Less polar derivatives may serve as valuable leads toward a potent and safe resistance modulator. Biological significance of the resistance-increasing activity of the most abundant phytoecdysteroids including 20-hydroxyecdysone is yet to be clarified.
• Synthesis of silenosterone, an insect-molting hormone
  作者：N. Z. Mamadalieva、N. Sh. Ramazanov、Z. Saatov

  DOI：10.1007/bf02236295

  日期：1999.11

  Silenosterone is synthesized in five steps: acetylation of 2-desoxy-alpha-ecdysone (1), saponification of 2-desoxy-alpha-ecdysone-3,22-diacetate (2) to the 22-monoacetate (3), and oxidation of the latter to a ketone (4) and its base hydrolysis (5). The structures of the compounds are confirmed by PMR, IR spectroscopy, and mass spectrometry.
• Phytoecdysteroids from Dianthus superbus L.: Structures and anti-neuroinflammatory evaluation
  作者：Xue-Li Hou、Yu-Qi Gao、Jing-Hui Yang、Han-Wu Liu、Meng-Meng Bai、Zhen-Hai Wu、Chun-Huan Li、Jun-Mian Tian、Jin-Ming Gao

  DOI：10.1016/j.phytochem.2023.113710

  日期：2023.8

  from the whole plant of Dianthus superbus L. Their structures were identified by extensive spectroscopy, mass spectrometric methods, chemical transformations, chiral HPLC analysis, and the single-crystal X-ray diffraction analysis. Superecdysones A and B possess a tetrahydrofuran ring in the side chain and superecdysones C–E are rare phytoecdysones containing a (R)-lactic acid moiety, whereas superecdysone

  六种未描述的 C 27 -植物蜕皮甾体衍生物，命名为超蜕皮激素 A-F，和十种已知的类似物是从石竹全株中提取的。它们的结构通过广泛的光谱学、质谱法、化学转化、手性 HPLC 分析和单晶X射线衍射分析。超蜕皮激素 A 和 B 在侧链上有一个四氢呋喃环，而超蜕皮激素 C-E 是罕见的植物蜕皮激素，含有 ( R)-乳酸部分，而超蜕皮激素 F 是一种不常见的 B 环修饰蜕皮激素。值得注意的是，基于超蜕皮激素 C 的可变温度（从 333 K 到 253 K）NMR 实验，缺失的碳信号在 253 K 处可见并已分配。评估了所有化合物的神经炎症生物测定，22-acetyl-2-deoxyecdysone, 2-deoxy-20-hydroxyecdysone, 20-hydroxyecdysone, ecdysterone-22- O-benzoate, 20-hydroxyecdysone - 20,22-