3β-acetoxy-16α-bromoandrost-5-en-17-one | 24335-49-7

• 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: 3β-acetoxy-16α-bromoandrost-5-en-17-one
• 英文别名: 3β-acetoxy-16α-bromo-androst-5-en-17-one；3β-Acetoxy-16α-brom-androst-5-en-17-on；16α-Brom-3β-acetoxy-17-oxo-androsten-(5)；[(3S,8R,9S,10R,13S,14S,16R)-16-bromo-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 24335-49-7
• 化学式: C₂₁H₂₉BrO₃
• 分子量: 409.363
• InChiKey: SMJCXQBAPTXOIC-TYINLYHXSA-N

物化性质

• 熔点：
  186 °C(Solv: acetone (67-64-1); methanol (67-56-1))
• 沸点：
  468.6±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-16α-bromoandrost-5-en-17-one 在 吡啶 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.25h， 生成 3beta,16alpha-Dicarbomethoxyandrost-5-en-17-one
  参考文献：
  名称：

  C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists

  摘要：

  Dehydroepiandrosterone (DHEA), the most abundant steroid in human circulating blood, is metabolized to sex hormones and other C-19-steroids. Our previous collaborative study demonstrated that androst-5-ene-3 beta,17 beta-diol (Adiol) and androst-4-ene-3,17-dione (Adione), metabolites of DHEA, can activate androgen receptor (AR) target genes. Adiol is maintained at a high concentration in prostate cancer tissue; even after androgen deprivation therapy and its androgen activity is not inhibited by the antiandrogens currently used to treat prostate cancer patients. We have synthesized possible metabolites of DHEA and several synthetic analogues and evaluated their role in androgen receptor transactivation to identify AR modulators. Steroids with low androgenic potential in PC-3 cell lines were evaluated for anti-dihydrotestosterone (DHT) and anti-Adiol activity. We discovered three potent antiandrogens: 3 beta-acetoxyandrosta-1,5-diene-17-one 17-ethylene ketal (ADEK), androsta-1,4-diene-3,17-dione 17-ethylene ketal (OAK), and 3 beta-hydroxyandrosta-5,16-diene (HAD) that antagonized the effects of DHT as well as of Adiol on the growth of LNCaP cells and on the expression of prostate-specific antigen (PSA). In vivo tests of these compounds will reveal their potential as potent antiandrogens for the treatment of prostate cancer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.022
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 sodium hydroxide 、 重氧水 、 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 3β-acetoxy-16α-bromoandrost-5-en-17-one
  参考文献：
  名称：

  Stereospecific synthesis of 16.alpha.-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism

  摘要：

  DOI：

  10.1021/jo00142a004

文献信息

• Steroidal aminothiazoles
  作者：Panayotis Catsoulacos、Dimitrios Kallias

  DOI：10.1002/jhet.5570160430

  日期：1979.6

  The treatment of 16α-bromo-17-ketosteroids and 2-bromo-3-ketosteroids with thiourea in dimethylformamide give the corresponding 2′-formamidothiazolosteroids.

  用硫脲在二甲基甲酰胺中处理16α-溴17-酮类固醇和2-溴-3-酮类固醇可得到相应的2'-甲酰胺基咪唑类固醇。
• Fajkos; Sorm, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 766,777
  作者：Fajkos、Sorm

  DOI：——

  日期：——
• Ellis et al., Journal of the Chemical Society, 1958, p. 800,802
  作者：Ellis et al.

  DOI：——

  日期：——
• Marquet,A.; Jacques,J., Bulletin de la Societe Chimique de France, 1962, p. 90 - 96
  作者：Marquet,A.、Jacques,J.

  DOI：——

  日期：——