(22S,23S)-3α,5-cyclostigmasta-6β,22,23-triol | 133304-25-3

• 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)-3α,5-cyclostigmasta-6β,22,23-triol
• 英文别名: (2S,3S,4S,5S)-5-ethyl-2-[(1S,2R,5R,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]-6-methylheptane-3,4-diol
• CAS: 133304-25-3
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: QRJGJZAQKHDENQ-AFXZUKNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (22S,23S)-3α,5-cyclostigmasta-6β,22,23-triol 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以78%的产率得到(22S,23S)-3β-chlorostigmast-5-ene-22,23-diol
  参考文献：
  名称：

  Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity

  摘要：

  In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-alpha production by macrophages. A preliminary qualitative structure-activity relationship was established. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.012
• 作为产物：
  描述：

  (22E)-3α,5-cyclo-6β-hydroxy-5α-stigmast-22-ene 在 四氧化锇 、 甲基磺酰胺 、 dihydroquinidine 9-O-(4-chlorobenzoate) 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 反应 144.0h， 以40%的产率得到(22R,23R)-3α,5-cyclo-stigmastane-6β,22,23-triol
  参考文献：
  名称：

  Synthesis of new Δ5-7-oxygenated and Δ5,7-unsaturated brassinosteroid analogs

  摘要：

  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.

  DOI：

  10.1016/s0039-128x(97)00008-1

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.
• Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity
  作者：Javier A. Ramírez、Andrea C. Bruttomesso、Flavia M. Michelini、Sofía L. Acebedo、Laura E. Alché、Lydia R. Galagovsky

  DOI：10.1016/j.bmc.2007.09.012

  日期：2007.12

  In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-alpha production by macrophages. A preliminary qualitative structure-activity relationship was established. (c) 2007 Elsevier Ltd. All rights reserved.