(20R,22R)-14-hydroperoxy-2β,3β,20,22,25-pentaexahydroxy-5β-cholest-7-en-6-one | 115040-67-0

• 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: (20R,22R)-14-hydroperoxy-2β,3β,20,22,25-pentaexahydroxy-5β-cholest-7-en-6-one
• 英文别名: 14α-hydroperoxy-20-hydroxyecdysone；14α-hydroperoxy-20-hydroxy-α-ecdysone；14-hydroperoxy-20-hydroxyecdysone；14alpha-Hydroperoxy-20-hydroxyecdysone；2β,3β,20,22,25-pentahydroxy-14α-hydroperoxy-5β-cholest-7-en-6-one；14-desoxy-14α-hydroperoxy-20-hydroxyecdysone；14α-hydroperoxy-14-deoxy-20-hydroxyecdysone；(2S,3R,5R,9R,10R,13R,14S,17S)-14-hydroperoxy-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 115040-67-0
• 化学式: C₂₇H₄₄O₈
• 分子量: 496.642
• InChiKey: JPJORQUJRURVBJ-YPVLXUMRSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  721.7±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (20R,22R)-14-hydroperoxy-2β,3β,20,22,25-pentaexahydroxy-5β-cholest-7-en-6-one 在 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成 蜕皮激素
  参考文献：
  名称：

  Fe（II）诱导的γ-羟基-α，β-烯酮裂解反应。的13部分1.合成（148） -的abeo- -Steroids

  摘要：

  通过Fe（II）诱导的14α-hydroperoxy-7-en-6-one的重排（串联β-裂变/还原烷基化）合成了一些体现迄今未知的13（148）-abeo骨架的甾体类似物。通过对NMR光谱的彻底分析来进行构型分配。通过X射线单晶分析明确评估了其中一种产品的结构。

  DOI：

  10.1002/hlca.19870700320
• 作为产物：
  描述：

  (20R,22R)-2β,3β,20,22,25-pentahydroxy-5β-cholest-8(14)-en-6-one 在 tetrafluoroboric acid 、 3 A molecular sieve 、 草酸 作用下， 以 甲醇 为溶剂， 反应 9.5h， 生成 (20R,22R)-14-hydroperoxy-2β,3β,20,22,25-pentaexahydroxy-5β-cholest-7-en-6-one
  参考文献：
  名称：

  Fe（II）诱导的γ-羟基-α，β-烯酮裂解反应。的13部分1.合成（148） -的abeo- -Steroids

  摘要：

  通过Fe（II）诱导的14α-hydroperoxy-7-en-6-one的重排（串联β-裂变/还原烷基化）合成了一些体现迄今未知的13（148）-abeo骨架的甾体类似物。通过对NMR光谱的彻底分析来进行构型分配。通过X射线单晶分析明确评估了其中一种产品的结构。

  DOI：

  10.1002/hlca.19870700320

文献信息

• Diversity-oriented synthesis through gamma radiolysis: Preparation of unusual ecdysteroid derivatives activating Akt and AMPK in skeletal muscle cells
  作者：Halima Meriem Issaadi、Zoltán Béni、Tünde Tóth、Miklós Dékány、Tusty-Jiuan Hsieh、György Tibor Balogh、Attila Hunyadi

  DOI：10.1016/j.bioorg.2021.104951

  日期：2021.7

  beneficial, non-hormonal bioactivities in mammals including humans. Gamma irradiations of aqueous solutions of 20E were conducted either in N2- or N2O-saturated solutions. Centrifugal partition chromatography was used to fractionate crude resulting irradiated materials using a biphasic solvent system composed of tert-butyl alcohol - ethyl acetate - water (0.45:0.9:1, v/v/v) in ascending mode. Subsequently

  伽马射线辐射是诱导生物活性化合物化学转化的一种独特方式。在本研究中，我们采用这种方法以多样性为导向合成 20-羟基蜕皮激素 (20E) 的类似物，这是一种丰富的蜕皮甾体，在包括人类在内的哺乳动物中具有一系列有益的非激素生物活性。20E水溶液的伽马辐射在N 2 -或N 2 O-饱和溶液中进行。离心分配色谱法用于使用由叔丁醇组成的双相溶剂系统来分级粗得到的辐照材料。- 丁醇 - 乙酸乙酯 - 水（0.45:0.9:1，v/v/v）在上升模式。随后，产物通过RP-HPLC纯化。分离出 14 种蜕皮甾体，包括 5 种新化合物，并通过一维和二维 NMR 和 HRMS 阐明了它们的结构。化合物2 - 4，7，9，12和15是为它们增加C2C12的AKT-和AMPK磷酸化的能力进行测试鼠骨骼肌管体外。这些化合物对 Akt 的活性与其母体化合物相似。Stachysterone B ( 7 ) 和一种新的环重排化合物
• Δ8(14)-14α-deoxy- and 14α-deoxy-14α-hydroperoxyecdysteroids
  作者：A. Sh. Ibragimova、N. A. Ves’kina、I. V. Galyautdinov、V. N. Odinokov

  DOI：10.1134/s1070428010110205

  日期：2010.11

  Delta(8(14))-14 alpha-deoxy-and 14 alpha-deoxy-14 alpha-hydroperoxyecdysteroids were synthesized, the reduction of Delta(8(14))-14 alpha-deoxy-20-hydroxyecdysone diacetonide at treatment with complex hydrides of alkali metals was investigated, and the stereochemistry of the obtained 6-hydroxy derivative and its acetate was established.
• Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton
  作者：V. N. Odinokov、I. V. Galyautdinov、A. Sh. Ibragimova、N. A. Veskina、L. M. Khalilov、F. M. Dolgushin、Z. A. Starikova

  DOI：10.1007/s10593-008-0157-7

  日期：2008.9

  The reaction of ecdysteroids (20-hydroxyecdysone and its acetonides) with lithium in liquid ammonia gave novel analogs with an oxetane 9 alpha,14 alpha-oxacycle in the steroid skeleton. In aqueous alcohol solution the 9,14-oxa analogs rearrange to the more stable 9 alpha,13 alpha-oxa analogs through a 1,2-migration of the 18-Me group from the C-13 to the C-14 atom.
• Lesma, Giordano; Nali, Micaela; Palmisano, Giovanni, Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 857 - 858
  作者：Lesma, Giordano、Nali, Micaela、Palmisano, Giovanni、Tollari, Stefano

  DOI：——

  日期：——
• Photochemical transformation of 20-hydroxyecdysone: production of monomeric and dimeric ecdysteroid analogues
  作者：Juraj Harmatha、Miloš Buděšínský、Karel Vokáč

  DOI：10.1016/s0039-128x(01)00140-4

  日期：2002.2

  Structural modification of 20-hydroxyecdysone (20E) based on photochemical trans formation yielded dimeric ecdysteroid 7alphaH,7'alphaH-bis-[(20R,22R)-20,3p,2beta,3beta,20,22,25-pentahydroxy-5beta-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and t4-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the B-II-bioassay compared with the original 20E. (C) 2002 Elsevier Science Inc. All rights reserved.