2-dehydro-3-epi-20-hydroxyecdysone

• 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-dehydro-3-epi-20-hydroxyecdysone
• 英文别名: (3S,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,3,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-2,6-dione
• 化学式: C₂₇H₄₂O₇
• 分子量: 478.626
• InChiKey: RRGYPIOLUPMGCP-FJWASMFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  蜕皮激素	20-Hydroxyecdysone	5289-74-7	C27H44O7	480.642

反应信息

• 作为反应物：
  描述：

  L-Selectride 、 2-dehydro-3-epi-20-hydroxyecdysone 以 四氢呋喃 为溶剂， 反应 2.0h， 以20%的产率得到2,3-diepi-20-hydroxyecdysone
  参考文献：
  名称：

  A short way to invert configuration of the 2,3-hydroxy groups in ecdysteroids

  摘要：

  3-epi-2-Dehydro-20-hydroxyecdysone and its 20,22-acetonide were reduced with lithium tris(secbutyl) hydridoborate selectively at the 2-oxo group with formation of 2 beta,3 beta-dihydroxy derivatives and the corresponding 2 alpha,3 alpha epimers which were separated by chromatography.

  DOI：

  10.1134/s1070428013070063
• 作为产物：
  描述：

  蜕皮激素 在 氧气 、 臭氧 作用下， 以 吡啶 为溶剂， 反应 0.33h， 以43%的产率得到2-dehydro-3-epi-20-hydroxyecdysone
  参考文献：
  名称：

  Regio- and stereodirected transformation of 20-hydroxyecdysone to 2-dehydro-3-epi-20-hydroxyecdysone under ozonization in pyridine

  摘要：

  A minor ecdysteroid from Froelichia floridana, namely, 2-dehydro-3-epi-20-hydroxyecdysone has been obtained by the one stage ozonization of 20-hydroxyecdysone in pyridine.

  DOI：

  10.1016/j.mencom.2008.07.006

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
• Biotransformations of 20-hydroxyecdysone and analogues by Curvularia lunata NRRL 2178
  作者：Chatchawan Changtam、Oratai Sukcharoen、Boon-ek Yingyongnarongkul、Apichart Suksamrarn

  DOI：10.1016/j.steroids.2006.06.002

  日期：2006.10

  20-Hydroxyecdysone, the arthropod moulting hormone, was biotransformed by the fungus Curvularia lunata NRRL 2178 to the rare ecdysteroid, 2-dehydro-3-epi-20-hydroxyecdysone, and the novel 3 alpha,9 alpha-cyclo ecdysteroid analogue, (20R,22R)-3 beta,14 alpha,20,22,25-pentahydroxy-3 alpha,9 alpha-cyclo-5 beta-cholest-7-en-2,6-dione in 14 and 44% yields, respectively. Ponasterone A and pterosterone were similarly biotransformed to the corresponding 2-dehydro-3-epi- and 3 alpha,9 alpha-cyclo-analogues. (c) 2006 Elsevier Inc. All rights reserved.
• Synthesis of 2-Dehydro-3-epi-20-hydroxyecdysone
  作者：Siritron Charoensuk、Boon-ek Yingyongnarongkul、Apichart Suksamrarn

  DOI：10.1016/s0040-4020(00)00845-0

  日期：2000.11

  2-Dehydro-3-epi-20-hydroxyecdysone a novel ecdysteroid isolated from Froelichia floridana, has bean partially synthesized from the readily available ecdysteroid, 20-hydroxyecdysone. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Regio- and stereodirected transformation of 20-hydroxyecdysone to 2-dehydro-3-epi-20-hydroxyecdysone under ozonization in pyridine
  作者：Rimma G. Savchenko、Yana R. Urmanova、Ruslan V. Shafikov、Svetlana R. Afon’kina、Leonard M. Khalilov、Victor N. Odinokov

  DOI：10.1016/j.mencom.2008.07.006

  日期：2008.7

  A minor ecdysteroid from Froelichia floridana, namely, 2-dehydro-3-epi-20-hydroxyecdysone has been obtained by the one stage ozonization of 20-hydroxyecdysone in pyridine.
• A short way to invert configuration of the 2,3-hydroxy groups in ecdysteroids
  作者：R. G. Savchenko、S. A. Kostyleva、V. V. Kachala、L. M. Khalilov、V. N. Odinokov

  DOI：10.1134/s1070428013070063

  日期：2013.7

  3-epi-2-Dehydro-20-hydroxyecdysone and its 20,22-acetonide were reduced with lithium tris(secbutyl) hydridoborate selectively at the 2-oxo group with formation of 2 beta,3 beta-dihydroxy derivatives and the corresponding 2 alpha,3 alpha epimers which were separated by chromatography.