(22R,23R)-3β,22,23-trihydroxystigmast-5-en-7-one | 191151-45-8

• 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: (22R,23R)-3β,22,23-trihydroxystigmast-5-en-7-one
• 英文别名: (3beta,22r,23r)-7-Ketostigmast-5-en-3,22,23-triol；(3S,8S,9S,10R,13R,14S,17R)-17-[(2S,3R,4R,5S)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 191151-45-8
• 化学式: C₂₉H₄₈O₄
• 分子量: 460.698
• InChiKey: BSFNEZGCJQLGLA-SHGRAUEJSA-N

物化性质

• 熔点：
  136 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  608.6±40.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (22R,23R)-3β,22,23-trihydroxystigmast-5-en-7-one 在 对甲苯磺酸 作用下， 反应 0.17h， 以79%的产率得到(22R,23R)-3β-hydroxy-22,23-isopropylidenedioxystigmast-5-en-7-one
  参考文献：
  名称：

  Δ5-7-Ketosterols with modified side chain: The synthesis and the effects on viability and cholesterol biosynthesis in Hep G2 cells

  摘要：

  合成的化合物包括：(22E)-30-羟基新植物甾-5,22-二烯-7-酮，(22R,23R)-3β,22,23-三羟基新植物甾-5-烯-7-酮，以及(22R,23R)-30-羟基-22,23-异丙基叉二氧基新植物甾-5-烯-7-酮。研究了所得的7-酮类固醇、7-酮胆固醇，以及(22S,23S)-3β-羟基-22,23-氧化新植物甾-5-烯-7-酮在肝癌细胞株Hep G2中的细胞毒性和对胆固醇生物合成的影响。

  DOI：

  10.1134/s1068162006050141
• 作为产物：
  描述：

  (22R,23R)-3β,22,23-triacetoxystigmast-5-ene 在 potassium dichromate 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.33h， 生成 (22R,23R)-3β,22,23-trihydroxystigmast-5-en-7-one
  参考文献：
  名称：

  Δ5-7-Ketosterols with modified side chain: The synthesis and the effects on viability and cholesterol biosynthesis in Hep G2 cells

  摘要：

  合成的化合物包括：(22E)-30-羟基新植物甾-5,22-二烯-7-酮，(22R,23R)-3β,22,23-三羟基新植物甾-5-烯-7-酮，以及(22R,23R)-30-羟基-22,23-异丙基叉二氧基新植物甾-5-烯-7-酮。研究了所得的7-酮类固醇、7-酮胆固醇，以及(22S,23S)-3β-羟基-22,23-氧化新植物甾-5-烯-7-酮在肝癌细胞株Hep G2中的细胞毒性和对胆固醇生物合成的影响。

  DOI：

  10.1134/s1068162006050141

文献信息

• Synthesis of new Δ5-7-oxygenated and Δ5,7-unsaturated brassinosteroid analogs
  作者：Bernhard Hellrung、Brunhilde Voigt、Jürgen Schmidt、Günter Adam

  DOI：10.1016/s0039-128x(97)00008-1

  日期：1997.5

  We report on the synthesis of the brassinosteroid analogs (22R,23R)-3 beta,7 beta,22,23-tetrahydroxy-stigmast-5-ene (13), (22R,23R)-3 beta,7 alpha,22,23-tetrahydroxy-stigmast-5-ene (15), and (22R,23R)-3 beta-22,23-trihydroxy-stigmast- 5,7-diene (18) by means of the osmium-catalyzed asymmetric dihydroxylation of intermediate 1, available from stigmasterol. This reaction sequence produced the expected (22S,23S)- and (22R,23R)-triols 6 and 7 as well as the 22,23-diketo derivatives 2 and 3. The phytohormone activity of the new brassinosteroid analogs is discussed. (C) 1997 by Elsevier Science Inc.
• Synthesis and cytotoxicity evaluation of 22,23-oxygenated stigmastane derivatives
  作者：Alexander Yu. Misharin、Arif R. Mehtiev、Galina E. Morozevich、Yaroslav V. Tkachev、Vladimir P. Timofeev

  DOI：10.1016/j.bmc.2007.10.056

  日期：2008.2.1

  Starting from (22E)-3 alpha,5 alpha-cyclo-6 beta-methoxystigmast-22-ene eighteen derivatives of (22S,23S)-22,23-oxidostigmastane, (22R,23R)-22,23-oxidostigmastane, and (22R,23R)-22,23-dihydroxystigmastane were synthesized and screened for cytotoxicity in human hepatoma Hep G2 cells and human breast carcinoma MCF-7 cells using MTT assay. Four compounds of this series exhibited high cytotoxicity in both cells; three compounds were selectively toxic in MCF-7 cells, one compound was toxic in Hep G2 cells, rather than in MCF-7 cells; four compounds at low concentrations increased MTT test values over the control. (C) 2007 Elsevier Ltd. All rights reserved.