17β-hydroxyandrosta-3,5-dien-7-one | 60397-50-4

• 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: 17β-hydroxyandrosta-3,5-dien-7-one
• 英文别名: 17beta-Hydroxyandrosta-3,5-dien-7-one；(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
• CAS: 60397-50-4
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: SHXCMOUXXLQOEC-YQAXKJAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17β-hydroxyandrosta-3,5-dien-7-one 生成 estra-3,5-diene-7,17-dione
  参考文献：
  名称：

  甾体3,5-二烯。

  摘要：

  DOI：

  10.1021/jm00234a009
• 作为产物：
  描述：

  3beta,17beta-二(乙酰氧基)-雄甾-5-烯-7-酮 在 氢氧化钾 作用下， 生成 17β-hydroxyandrosta-3,5-dien-7-one
  参考文献：
  名称：

  US2170124

  摘要：

  公开号：

文献信息

• Ergosteroids VII: perchloric acid-induced transformations of 7-oxygenated steroids and their bio-analytical applications—a liquid chromatographic-mass spectrometric study
  作者：Ashok Marwah、Padma Marwah、Henry Lardy

  DOI：10.1016/s0045-2068(02)00010-x

  日期：2002.8

  Sulfate esters of 7-oxo-delta(5)-steroids can be selectively and quantitatively hydrolyzed to the corresponding free steroids in the presence of carboxylic acid esters by solvolysis with perchloric acid in ethyl acetate at room temperature. Sulfates as well as carboxylic acid esters, methyl ethers, and ketals can be quantitatively converted to the corresponding 3,5-diene-7-one derivatives by heating

  通过在室温下用高氯酸在乙酸乙酯中进行溶剂分解，可以在羧酸酯存在下将7-氧代-δ（5）-甾族化合物的硫酸酯选择性地和定量地水解为相应的游离甾体。通过在65°C的甲醇中与高氯酸加热，可以将硫酸盐以及羧酸酯，甲基醚和缩酮定量转化为相应的3,5-二烯-7-一衍生物。二烯具有较强的紫外线吸收能力最大中心在284 nm附近。这些反应已用于表征和解析结构复杂的生物基质中存在的7-氧化的delta（5）-类固醇，也可用于定量估计总的7-oxo-delta（5）-类固醇（在生物基质中是游离的还是结合的）。
• Therapeutic treatment of androgen receptor driven conditions
  申请人：Hollis-Eden Pharmaceuticals Inc.

  公开号：EP1832598A2

  公开（公告）日：2007-09-12

  The invention provides methods to treating conditions such as prostate cancer, or for ameliorating one or more symptoms associated with prostate cancer, or for agents that modulate the biological activity of the androgen receptor. The invention also provides methods and compositions suitable for therapeutic applications.

  本发明提供了治疗前列腺癌等疾病的方法，或改善与前列腺癌相关的一种或多种症状的方法，或调节雄激素受体生物活性的制剂。本发明还提供了适用于治疗应用的方法和组合物。
• Androstenol derivatives as androgen receptor modulator
  申请人：Harbor BioSciences, Inc.

  公开号：EP2322182A1

  公开（公告）日：2011-05-18

  The invention provides methods to treating conditions such as prostate cancer, or for ameliorating one or more symptoms associated with prostate cancer, or for agents that modulate the biological activity of the androgen receptor. The invention also provides methods and compositions suitable for therapeutic applications.

  本发明提供了治疗前列腺癌等疾病的方法，或改善与前列腺癌相关的一种或多种症状的方法，或调节雄激素受体生物活性的制剂。本发明还提供了适用于治疗应用的方法和组合物。
• C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists
  作者：Padma Marwah、Ashok Marwah、Henry A. Lardy、Hiroshi Miyamoto、Chawnshang Chang

  DOI：10.1016/j.bmc.2006.05.022

  日期：2006.9

  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.
• Butenandt; Hausmann; Paland, Chemische Berichte, 1938, vol. 71, p. 1316,1321
  作者：Butenandt、Hausmann、Paland

  DOI：——

  日期：——