5α-pregnane-3,6,20-trione | 1923-27-9

• 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: 5α-pregnane-3,6,20-trione
• 英文别名: 5α-pregn-3,6,20-trione；5α-Pregnan-3,6,20-trion；5α-Pregnantrion-(3.6.20)；5α-Pregnantrion-(3,6,20)；Allopregnan-3,6,20-trion；5alpha-Pregnane-3,6,20-trione；(5S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
• CAS: 1923-27-9
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: MRURHGKZPVRRKA-UBYIZVQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-pregnane-3,6,20-trione 在 溶剂黄146 、 铂 作用下， 生成 Pregnane-3,6,20-triol, (3b,5a,6b,20R)-
  参考文献：
  名称：

  Sterols. CXXX. 3,6-Diketo Sterols and their Reduction Products^*

  摘要：

  DOI：

  10.1021/ja01254a006
• 作为产物：
  描述：

  孕烯醇酮 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 5α-pregnane-3,6,20-trione
  参考文献：
  名称：

  Sterols. CXI. Sapogenins. XL. The Conversion of Chlorogenin to Tigogenin

  摘要：

  DOI：

  10.1021/ja01868a032

文献信息

• The synthesis and characterisation of some 13,6,20-trioxygenated pregnane derivatives
  作者：J ALLEN、B KNIGHTS

  DOI：10.1016/s0039-128x(68)80071-6

  日期：1968.4

  Abstract A pregnane-3,6,20-triol isomer has been isolated from hydrolysed urine. In order to identify this compound and to facilitate further study four pregnane-3,6,20β-triol isomers have been synthesised starting from 3α,6α-dihydroxy-5β-pregnan-20-one. Gas chromatographic and mass spectrometric data have been recorded for these compounds and also g.l.c. data for the corresponding 20α-isomers. The

  摘要 从水解尿液中分离出一种孕烷-3,6,20-三醇异构体。为了鉴定该化合物并促进进一步研究，从 3α,6α-dihydroxy-5β-pregnan-20-one 开始合成了四种孕烷-3,6,20β-三醇异构体。已经记录了这些化合物的气相色谱和质谱数据以及相应 20α-异构体的 glc 数据。后者与相应的 20β-异构体、17α-20-酮和起始材料一起通过 20-酮的非选择性还原获得。
• Synthesis and biological evaluation of steroidal derivatives as selective inhibitors of AKR1B10
  作者：Wei Zhang、Ling Wang、Liping Zhang、Wenli Chen、Xinying Chen、Minyu Xie、Guangmei Yan、Xiaopeng Hu、Jun Xu、Jingxia Zhang

  DOI：10.1016/j.steroids.2014.04.010

  日期：2014.8

  AKR1B10 is a member of human aldo-keto reductase superfamily, and a promising anti-cancer therapeutic target. In this paper, androst-5-ene-3 beta-ol, dehydroepiandrosterone, pregnenolone and cholesterol were used as reactants, sixteen products were obtained through Jones reaction and reduction reaction using NaBH4. Their inhibitory activities against AKR1B10 and AKR1B1 were measured. The most active compound (3a) has the IC50 of 0.50 mu M for AKR1B10, and the most AKR1B10 selective compound (2a) has the IC50 of 0.81 mu M with AKR1B1/AKR1B10 selectivity of 195. In addition, the binding modes of 2a and 3a in the active site of human AKR1B10 were identified by docking. (C) 2014 Elsevier Inc. All rights reserved.
• Degradation of Hyodesoxycholic Acid
  作者：Robert Bruce Moffett、James E. Stafford、Jacob Linsk、Willard M. Hoehn

  DOI：10.1021/ja01213a052

  日期：1946.9
• Sapogenin transformation products and preparation of same
  申请人：PARKE DAVIS & CO

  公开号：US02352852A1

  公开（公告）日：1944-07-04
• Investigations on steroids. XX. 6β- and 6α-Acetoxy- and Hrdroxy-Derivatives of Progesterone and Androstenedione
  作者：Charles P. Balant、Maximilian Ehrenstein

  DOI：10.1021/jo50012a005

  日期：1952.12