(2S,3R,5R,9S,10S,13R,14S,17S)-17-acetyl-2,3,9,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | 1224637-80-2

• 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: (2S,3R,5R,9S,10S,13R,14S,17S)-17-acetyl-2,3,9,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
• CAS: 1224637-80-2
• 化学式: C₂₁H₃₀O₆
• 分子量: 378.466
• InChiKey: XVZVJPJVOAPTLG-GERHNTSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1S,3aS,5aR,6aR,9aS,10aS,10bS,12aR)-1-acetyl-3a,10b-dihydroxy-8,8,10a,12a-tetramethyl-1,2,3,3a,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one 在 水 、 溶剂黄146 作用下， 以74%的产率得到(2S,3R,5R,9S,10S,13R,14S,17S)-17-acetyl-2,3,9,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
  参考文献：
  名称：

  Stereoselective synthesis of 9α-hydroxylated ecdysteroids

  摘要：

  Treatment of ecdysteroids with excess of TBAF in THF was shown to proceed with stereoselective oxidation at the 9 alpha position of the carbon skeleton. The stereochemistry of the products was confirmed by X-ray analysis. Using this method. 9 alpha-hydroxyecdysteroids were obtained in good yield. The results open a route to novel type of natural and modified steroids that are difficult to access otherwise. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.10.011

文献信息

• Side-chain cleaved phytoecdysteroid metabolites as activators of protein kinase B
  作者：Halima Meriem Issaadi、József Csábi、Tusty-Jiuan Hsieh、Tamás Gáti、Gábor Tóth、Attila Hunyadi

  DOI：10.1016/j.bioorg.2018.10.049

  日期：2019.2

  Phytoecdysteroids exert their non-hormonal anabolic and adaptogenic effects in mammals, including humans, through a partially revealed mechanism of action involving the activation of protein kinase B (Akt). We have recently found that poststerone, a side-chain cleaved in vivo metabolite of 20-hydroxyecdysone, exerts potent anabolic activity in rats.Here we report the semi-synthetic preparation of a series of side-chain cleaved ecdysteroids and their activity on the Akt phosphorylation in murine skeletal muscle cells. Twelve C-21 ecdysteroids including 8 new compounds were obtained through the oxidative side-chain cleavage of various phytoecdysteroids, or through the base-catalyzed autoxidation of poststerone. The complete H-1 and C-13 NMR spectroscopic assignments of the new compounds are presented. Among the tested compounds, 9 could activate Akt stronger than poststerone revealing that side-chain cleaved derivatives of phytoecdysteroids other than 20-hydroxyecdysone are valuable bioactive metabolites. Thus, our results suggest that the expectable in vivo formation of such compounds should contribute to the bioactivity of herbal preparations containing ecdysteroid mixtures.