5α-androst-3β,6β,17β-triol | 19316-60-0

• 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-androst-3β,6β,17β-triol
• 英文别名: 5α-androstane-3β,6β,17β-triol；5α-Androstan-3β,6β,17β-triol；(3S,5S,6R,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,17-triol
• CAS: 19316-60-0
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: OFAZPSYXUKIJIK-AWOFKVEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  5α-androst-3β,6β,17β-triol 在 Jones reagent 作用下， 以85%的产率得到5α-androst-3,6,17-trione
  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
• 作为产物：
  描述：

  (3b,17b)-雄甾-5-烯-3,17-二醇 3,17-二乙酸酯 在 吡啶 、 硝酸 、 乙酸乙酯 、 铂 作用下， 生成 5α-androst-3β,6β,17β-triol
  参考文献：
  名称：

  50.潜在的致癌物。第一部分Δ 6 -Steroids

  摘要：

  DOI：

  10.1039/jr9530000245

文献信息

• 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.
• 50. Potential carcinogens. Part I. Δ⁶-Steroids
  作者：D. L. Garmaise、C. W. Shoppee

  DOI：10.1039/jr9530000245

  日期：——