5α-androstane-3,6-dione | 6563-99-1

• 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-androstane-3,6-dione
• 英文别名: (5S,8S,9S,10R,13S,14S)-10,13-dimethyl-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
• CAS: 6563-99-1
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: GNWJTKAFPYSBEZ-IJPPCXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-androstane-3,6-dione 以 乙醇 为溶剂， 反应 120.0h， 生成 16β,18-diacetoxy-5α-androstane-3,6-dione
  参考文献：
  名称：

  Denny, William A.; Fredericks, Peter M.; Ghilezan, Irene, Journal of Chemical Research, Miniprint, 1980, # 1, p. 345 - 360

  摘要：

  DOI：
• 作为产物：
  描述：

  雄甾-5-烯-3-醇 在 sodium tetrahydroborate 、 Jones reagent 、 cerium(III) chloride 、 nickel dichloride 作用下， 生成 5α-androstane-3,6-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of steroidal derivatives as selective inhibitors of AKR1B10

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2014.04.010

文献信息

• The biotransformation of some steroids by Cephalosporium aphidicola
  作者：James R. Hanson、Habib Nasir

  DOI：10.1016/0031-9422(93)85284-x

  日期：1993.7

  Abstract Hydroxylation of 5α-androstan-3-one and 3,6-dione by C. aphidicola takes place at C-17β and, in the case of the latter, at C-5α. The fungus reduces 5α-androstan-17-one and the 3,17-dione to the 17β-alcohols.

  摘要 C. aphidicola 对 5α-androstan-3-one 和 3,6-dione 的羟基化发生在 C-17β，在后者的情况下，发生在 C-5α。该真菌将 5α-androstan-17-one 和 3,17-dione 还原为 17β-醇。
• Long-Range Through-Bond Photoactivated σ Bond Cleavage in Steroids. Intramolecular Sensitized Debromination¹
  作者：Wen-Shan Li、Harry Morrison

  DOI：10.1021/ol990319s

  日期：2000.1.1

  [GRAPHICS]The photolysis of 17 alpha-bromo-3 alpha-(triphenylsilyloxy)-5 alpha-androstane (2; 3 alpha TPSO/17 alpha Br) and 17 alpha-bromo-3 alpha-(triphenylsilyloxy)-5 alpha-androstan-6- one (3; 3 alpha TPSO/6ketone/17 alpha Br) is described. Irradiation of 2 with 266 nm light leads to debromination via intramolecular transfer of triplet excitation energy with a quantum efficiency of 0.0011, Photolysis of 3 with both 266 and 308 nm light leads to debromination with quantum efficiencies of ca. 0.0066, The debromination of 3 is attributed to activation via the ketone excited singlet state, with singlet energy transfer from C6 to C17 ca, 35% efficient and occurring with a rate constant of 1.4 x 10(8) s(-1).
• 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.
• Denny, William A.; Fredericks, Peter M.; Ghilezan, Irene, Journal of Chemical Research, Miniprint, 1980, # 1, p. 345 - 360
  作者：Denny, William A.、Fredericks, Peter M.、Ghilezan, Irene、Jones, Ewart R. H.、Meakins, G. Denis、Miners, John O.

  DOI：——

  日期：——