20-hydroxyecdysone 20,22-acetonide 2-mesylate | 182422-96-4

• 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: 20-hydroxyecdysone 20,22-acetonide 2-mesylate
• 英文别名: [(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] methanesulfonate
• CAS: 182422-96-4
• 化学式: C₃₁H₅₀O₉S
• 分子量: 598.799
• InChiKey: SOEFIKRJRJQIST-CDHZUWMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  20-hydroxyecdysone 20,22-acetonide 2-mesylate 在 sodium tetrahydroborate 、 胍 乙酸盐 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 842.0h， 生成 3-epi-2-D-20-ECD
  参考文献：
  名称：

  3- Epi -2-deoxy-20-hydroxyecdysone及其类似物的合成和蜕皮激素活性

  摘要：

  次要的蜕皮甾体3-表位-2-脱氧-20-羟基蜕皮激素（3-表位-2-D-20-ECD）已由20-羟基蜕皮酮部分合成。还合成了2-D-5α-20-ECD和3-脱氢类似物3-脱氢-2-D-20-ECD和3-脱氢-2-D-5α-20-ECD。这些化合物的蜕皮激素活性已经使用Musca生物测定法进行了研究。

  DOI：

  10.1016/s0040-4020(97)00025-2
• 作为产物：
  描述：

  蜕皮激素 在 吡啶 、 对甲苯磺酸 作用下， 生成 20-hydroxyecdysone 20,22-acetonide 2-mesylate
  参考文献：
  名称：

  Stereoselective synthesis and moulting activity of 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5α-20-hydroxyecdysone

  摘要：

  The ecdysteroid analogues 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5alpha-20-hydroxyecdysone have been synthesized from the readily available ecdysteroid, 20-hydroxyecdysone, and moulting activity has been determined using the Musca bioassay. As expected, the 2,3-diepi-analogue was less active than the parent ecdysteroid, 20-hydroxyecdysone. However, the 2,3-diepi-5alpha-analogue, which was expected to be inactive in the assay, exhibited moulting activity though it was approximately 1.5-fold less active than its 5beta-analogue. The activity of the 5alpha-analogue could possibly result from the ability of this compound to bind to the ecdysteroid receptor. Alternatively, a possible in vivo C-5 epimerization of the 2,3-diepi-5alpha-analogue to the corresponding 5beta-analogue could account for its activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.042

文献信息

• Functional group-mediated biotransformation by Curvularia lunata NRRL 2178: synthesis of 3-dehydro-2-deoxy-ecdysteroids from the 3-hydroxy-2-mesyloxy analogues
  作者：Chatchawan Changtam、Oratai Sukcharoen、Boon-ek Yingyongnarongkul、Nitirat Chimnoi、Apichart Suksamrarn

  DOI：10.1016/j.tet.2008.01.033

  日期：2008.3

  Microbial transformation of ecdysteroids with 3-hydroxy-2-mesyloxy functional group by the fungus Curvularia lunata NRRL 2178 furnished 3-dehydro-2-deoxy analogues. The metabolites included 3-dehydro-2-deoxy analogues of 20-hydroxyecdysone, pterosterone, ponasterone A, 20-hydroxyecdysone 20,22-acetonide, shidasterone, and poststerone. The mild biotransformation conditions prevented the metabolites

  真菌 Curvularia lunata NRRL 2178 提供的 3-dehydro-2-deoxy 类似物对具有 3-hydroxy-2-mesyloxy 官能团的蜕皮甾体的微生物转化。代谢物包括 20-羟基蜕皮激素、蝶甾酮、松甾酮 A、20-羟基蜕皮激素 20,22-丙酮、shidasterone 和 poststerone 的 3-dehydro-2-deoxy 类似物。温和的生物转化条件阻止了代谢物的 C-5 差向异构化。
• Synthesis and biological activity of 2-deoxy-20-hydroxyecdysone and derivatives
  作者：Apichart Suksamrarn、Boon-ek Yingyongnarongkul

  DOI：10.1016/0040-4020(96)00750-8

  日期：1996.9

  The naturally occurring ecdysteroids 2-deoxy-20-hydroxyecdysone (2-D-20-ECD, 2-deoxycrustecdysone), 2-D-20-ECD 3-acetate (2-deoxyecdysterone 3-acetate), 2-D-20-ECD 22-acetate and 2-D-20-ECD 22-benzoate have been partially synthesized from 20-hydroxyecdysone. Moulting hormone activity of these ecdysteroids has been studied using the Musca bioassay.

  天然蜕皮类固醇2-脱氧20-羟基蜕皮酮（2-D-20-ECD，2-脱氧壳蜕皮酮），2-D-20-ECD 3-乙酸盐（2-脱氧蜕皮甾酮3-乙酸盐），2-D-20- ECD 22-乙酸盐和2-D-20-ECD 22-苯甲酸盐已由20-羟基蜕皮激素部分合成。这些蜕皮甾类的蜕皮激素活性已经使用Musca生物测定法进行了研究。
• [EN] ECDYSTEROID ANALOGUES HAVING PLANT GROWTH PROMOTING ACTIVITY<br/>[FR] ANALOGUES D'ECDYSTÉROÏDES AYANT UNE ACTIVITÉ FAVORISANT LA CROISSANCE VÉGÉTALE
  申请人：THAILAND RESERACH FUND

  公开号：WO2012053994A3

  公开（公告）日：2012-10-11
• Stereoselective synthesis and moulting activity of integristerone A and analogues
  作者：Saowanee Kumpun、Boon-ek Yingyongnarongkul、René Lafont、Jean-Pierre Girault、Apichart Suksamrarn

  DOI：10.1016/j.tet.2006.11.063

  日期：2007.1

  Integristerone A, a rare ecdysteroid of plant origin, has been synthesized from 20-hydroxyecdysone with 2-deoxy- 1,2-didehydro-20-hydroxyecdysone as the key intermediate, followed by stereoselective asymmetric dihydroxylation. The analogues 1,2-di-epi-integristerone A and 1,2-di-epi-5 alpha-integristerone A have also been synthesized. Integristerone A exhibited approximately 9-fold lower moulting activity than the parent 20-hydroxyecdysone in the Musca domestica bioassay, indicating that the presence of a 1 beta-hydroxyl group resulted in a decrease in activity. As expected, the 1,2-di-epi-5 alpha-analogue was inactive in this assay. (c) 2006 Elsevier Ltd. All rights reserved.