ergost-24(28)-ene-3β,5α,6β-triol | 59048-81-6

• 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: ergost-24(28)-ene-3β,5α,6β-triol
• 英文别名: (3S,5R,6R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol
• CAS: 59048-81-6
• 化学式: C₂₈H₄₈O₃
• 分子量: 432.687
• InChiKey: ZGVRWNYCQXZLTR-VJENCBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  ergost-24(28)-ene-3β,5α,6β-triol 在 chromium(VI) oxide 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 以20 mg的产率得到24-methylenecholestan-5α-ol-3,6-dione
  参考文献：
  名称：

  Pruna, L. B.; Henriques, Ruth D.; Huneck, S., Pharmazie, 1984, vol. 39, # 2, p. 117 - 120

  摘要：

  DOI：
• 作为产物：
  描述：

  24-oxocholesterol 在 正丁基锂 、 甲酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.58h， 生成 ergost-24(28)-ene-3β,5α,6β-triol
  参考文献：
  名称：

  Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking

  摘要：

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.03.004

文献信息

• Bortolotto,M. et al., Bulletin des Societes Chimiques Belges, 1976, vol. 85, p. 27 - 34
  作者：Bortolotto,M. et al.

  DOI：——

  日期：——
• Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking
  作者：Wenli Chen、Xinying Chen、Shujia Zhou、Hong Zhang、Ling Wang、Jun Xu、Xiaopeng Hu、Wei Yin、Guangmei Yan、Jingxia Zhang

  DOI：10.1016/j.steroids.2016.03.004

  日期：2016.6

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.
• Pruna, L. B.; Henriques, Ruth D.; Huneck, S., Pharmazie, 1984, vol. 39, # 2, p. 117 - 120
  作者：Pruna, L. B.、Henriques, Ruth D.、Huneck, S.、Schreiber, K.、Preiss, A.

  DOI：——

  日期：——