6α-fluoro-17β-hydroxy-5α-androstan-3-one | 1992-81-0

• 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: 6α-fluoro-17β-hydroxy-5α-androstan-3-one
• 英文别名: 6alpha-Fluoro-dihydrotestosterone；(5S,6S,8R,9S,10R,13S,14S,17S)-6-fluoro-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1992-81-0
• 化学式: C₁₉H₂₉FO₂
• 分子量: 308.436
• InChiKey: YUIAWFKQFLYPGL-ZXHZLALASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3-ethylenedioxy-6α-fluoro-17β-tetrahydropyranyloxy-5α-androstane 在 盐酸 作用下， 以 丙酮 为溶剂， 以95%的产率得到6α-fluoro-17β-hydroxy-5α-androstan-3-one
  参考文献：
  名称：

  Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging

  摘要：

  Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R 1881 = 100) for the androgen receptor and for sex steroid binding protein. Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6 alpha-fluoro-19-nor-testosterone (RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6 alpha-fluoro-19-nor-testosterone (RBA = 8.9 versus 6.6). Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the alpha-epimers compared to the corresponding beta-epimers (4:1-15:1). Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied. Based on the binding properties of compounds in this series, 6 alpha-fluoro-19-nor-testosterone appears to have the most promise as a turner imaging agent.

  DOI：

  10.1016/0039-128x(95)00009-f

文献信息

• Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging
  作者：Yearn Seong Choe、John A. Katzenellenbogen

  DOI：10.1016/0039-128x(95)00009-f

  日期：1995.5

  Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R 1881 = 100) for the androgen receptor and for sex steroid binding protein. Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6 alpha-fluoro-19-nor-testosterone (RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6 alpha-fluoro-19-nor-testosterone (RBA = 8.9 versus 6.6). Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the alpha-epimers compared to the corresponding beta-epimers (4:1-15:1). Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied. Based on the binding properties of compounds in this series, 6 alpha-fluoro-19-nor-testosterone appears to have the most promise as a turner imaging agent.