androst-4-ene-16α,17β-diol | 1080005-66-8

• 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: androst-4-ene-16α,17β-diol
• 英文别名: (8R,9S,10R,13S,14S,16R,17R)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-16,17-diol
• CAS: 1080005-66-8
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: DSYKSMXMQXYYEK-FPNLOETNSA-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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  16α-hydroxyandrosta-4-en-17-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以50%的产率得到androst-4-ene-16α,17β-diol
  参考文献：
  名称：

  Aromatization of androstenedione and 16α-hydroxyandrostenedione in human placental microsomes

  摘要：

  Inhibition of aromatase activity in human placental microsomes with androstenedione (AD) (1a) and its 19-oxygenated derivatives 1b and 1c, their 16a-hydroxy compounds 2 and 3, and 3-deoxyandrost-4-ene compounds 5 and 6 was studied using [1 beta-(3)H]AD as a substrate and compared to that with [1 beta-(3)H]16 alpha-hydroxyandrostenedione (16-OHAD). AD series of steroids, compounds 1, inhibited competitively [1 beta-(3)H]AD aromatization whereas other 16a-hydroxy steroids 2, 3, S, and 6 inhibited AD aromatization in a non-competitive manner. On the other hand, all of 16-OHAD series, compounds 2, blocked the [1 beta-(3)H]16-OHAD aromatization in a competitive manner whereas the AD series steroids 1 as well as the 3-deoxy-16 alpha-hydroxy-17-one steroids 5 and 3-deoxy-16 alpha,17 beta-diol steroids 6 inhibited 16-OHAD aromatization non-competitively. 3-Carbonyl and 16 alpha-hydroxy functions of 16-OHAD play a critical role of selection of the 16-OHAD binding site. The results suggest that the AD derivatives 1 are kinetically aromatized at a different site from the 16-OHAD derivatives 2. Physical and/or chemical environments around the aromatase protein in the microsomal membrane may play a significant role in the expression of the substrate specificity, and the present results do not exclude the idea that the placental microsomes have a single binding site. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.06.001