(22S,23S)-22,23-dihydroxy-3α,5-cyclo-5α-stigmastane-6-one | 104933-90-6

• 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: (22S,23S)-22,23-dihydroxy-3α,5-cyclo-5α-stigmastane-6-one
• 英文别名: (1S,2R,5R,7R,10S,11S,14R,15S)-14-[(2S,3S,4S,5S)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-2,15-dimethylpentacyclo[8.7.0.02,7.05,7.011,15]heptadecan-8-one
• CAS: 104933-90-6
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: ACAZGOGXMVEABK-UAUXHMQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (22S,23S)-22,23-dihydroxy-3α,5-cyclo-5α-stigmastane-6-one 在 吡啶溴化氢盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到(22S,23S,24S)-22,23-dihydroxy-5α-stigmast-2-en-6-one
  参考文献：
  名称：

  A convenient isomerization of 6-oxo-3α,5-cyclo-5α-steroids to 6-oxo-Δ2-5α-steroids

  摘要：

  Direct isomerization of 6-oxo-3 alpha,5-cyclo-5 alpha-steroids to 6-oxo-delta 2-5 alpha-steroids was accomplished by pyridinium hydrobromide in dimethyl-formamide.

  DOI：

  10.1016/0039-128x(85)90020-0
• 作为产物：
  描述：

  2-乙基-3-甲基-1-丁醇 在 吡啶 、 sodium amalgam 、 四氧化锇 、 正丁基锂 、 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 46.0h， 生成 (22S,23S)-22,23-dihydroxy-3α,5-cyclo-5α-stigmastane-6-one
  参考文献：
  名称：

  Synthesis of (24R)-homobrassinolide

  摘要：

  DOI：

  10.1007/bf00629972

文献信息

• Studies on steroidal plant growth regulators 22. Osmium tetroxide catalyzed asymmetric dihydroxylation of the (22E, 24R)- and the (22E, 24S)-24-Alkyl steroidal unsaturated side chain
  作者：Li-Qiang Sun、Wei-Shan Zhou、Xin-Fu Pan

  DOI：10.1016/s0957-4166(00)86139-x

  日期：1991.1

  The osmium tetroxide catalyzed asymmetric hydroxylation of the (22E, 24R)- and (22E, 24S)-24-alkyl steroidal unsaturated side chain are described. High stereoselectivity was obtained on dihydroxylation of these unsaturated side chains, when the 24-alkyl is methyl, while in the case of a 24-ethyl substituent the chiral ligand would be the dihydroquinine p-chlorobenzoate (DHQ).

  描述了四氧化催化的（22E，24R）-和（22E，24S）-24-烷基甾族不饱和侧链的不对称羟基化。当24-烷基为甲基时，通过这些不饱和侧链的二羟基化获得高的立体选择性，而在24-乙基取代基的情况下，手性配体将是对氯苯甲酸二氢奎宁（DHQ）。
• Huang, Liang-Fu; Zhou, Wei-Shan; Sun, Li-Qiang, Journal of the Chemical Society. Perkin transactions I, 1993, # 14, p. 1683 - 1686
  作者：Huang, Liang-Fu、Zhou, Wei-Shan、Sun, Li-Qiang、Pan, Xin-Fu

  DOI：——

  日期：——
• Toxicity of (22R,23R)-22,23-dihydroxystigmastane derivatives to cultured cancer cells
  作者：Alexander Yu. Misharin、Arif R. Mehtiev、Vladimir N. Zhabinskii、Vladimir A. Khripach、Vladimir P. Timofeev、Yaroslav V. Tkachev

  DOI：10.1016/j.steroids.2010.01.006

  日期：2010.3

  Toxicity of eight 22,23-dihydroxystigmastane derivatives (four pairs of (22R,23R)- and (22S,23S)-isomers differing in steroid backbone structure) to human breast Carcinoma MCF-7 cells was compared. For every pair of structurally related compounds, (22R,23R) isomer was found to be significantly more toxic than (22S,23S) isomer. Computational analysis showed that side chain of (22R,23R)-22,23-dihydroxystigmastane derivatives is rigid, whereas that of (22S,23S)-isomers is rather flexible. Structure of steroid backbone significantly affects cytotoxicity of (22R,23R)-22,23-dihydroxystigmastane derivatives to human breast carcinoma MCF-7 cells, human ovary carcinoma CaOv cells, and human prostate carcinoma LnCaP cells. (22R,23R)-3 beta,22,23-trihydroxystigmast-5-ene and (22R,23R)-3 beta,22,23-trihydroxystigmast-5-en-7-one, both comprising equatorial 3 beta-hydroxyl group, exhibited the highest cytotoxicity, while the most polar 28-homobrassinolide and 28-homocastasterone, both comprising 2 alpha,3 alpha-dihydroxy groups, exhibited the lowest toxicity. Binding of (22R,23R)22,23-dihydroxystigmastane derivatives to plasmatic membrane was suggested to be important for cytotoxicity. (C) 2010 Elsevier Inc. All rights reserved.
• 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.