3-羟基雄甾-4-烯-6,17-二酮 | 18386-45-3

• 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
• 中文名称: 3-羟基雄甾-4-烯-6,17-二酮
• 英文名称: 3β-hydroxyandrost-4-ene-6,17-dione
• 英文别名: androst-4-ene-3β-ol-6,17-dione；3β-Hydroxy-Δ⁴-androstendion-(6,17)；3-Hydroxyandrost-4-ene-6,17-dione；(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-6,17-dione
• CAS: 18386-45-3
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: ARAPFCZLRWLJAA-LZBOESDWSA-N

物化性质

• 熔点：
  193-196℃
• 密度：
  1.19

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基雄甾-4-烯-6,17-二酮 在 吡啶 作用下， 反应 20.83h， 生成 3-alpha-methoxyandrost-4-ene-6,17-dione
  参考文献：
  名称：

  竞争抑制和雄激素-4-烯-3,6-二酮衍生物和3α-甲氧基雄酮-4-烯-6,17-二酮对人胎盘芳香酶的杀灭作用。

  摘要：

  制备了Androst-4-ene-3,6-dione衍生物2-4和3α-甲氧基-4-en-6-一个甾体7，并测试了它们抑制人胎盘微粒体中芳香化酶的能力。该系列的16α-溴化物2、16α-醇3和3α-甲醇盐7是有效的芳香化酶竞争性抑制剂，表观Ki分别为150 nM，1.18 microM和700 nM。在烟酰胺腺嘌呤二核苷酸磷酸（NADPH）还原的情况下，化合物2导致时间依赖性芳香酶活性双相丧失，而化合物7导致活性的时间依赖性伪一阶失活，其激酶活性为0.417和0.036分钟对于化合物2和7-1。NADPH和氧气是时间依赖性灭活所必需的，在每种情况下，基质，rost-4-ene-3,17-dione都可以防止这种情况。

  DOI：

  10.1248/cpb.38.3076
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 氯化亚砜 、 己二酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 丁酮 、 苯 为溶剂， 反应 28.0h， 生成 3-羟基雄甾-4-烯-6,17-二酮
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n

文献信息

• Modified aromatase inhibitors having improved bioavailability
  申请人：Kneller W. Bruce

  公开号：US20050203074A1

  公开（公告）日：2005-09-15

  The present invention relates to the modification of 3-beta-hydroxyandrost-4-ene-6,17-dione (“3-OHAT”) and its metabolites/derivatives at either the 3 rd or 17 th carbon or 3 rd and 17 th carbons with various ethers and/or esters and to the modification of 3-beta-hydroxyandrost-4-ene-6,17-dione (“3-OHAT”) and its metabolites/derivatives at carbon 6 with a methyl, methoxy, methylene, hydroxymethylene or acetoxy functional group to improve and increase the oral bioavailability and/or plasma half life and/or efficacy in mammals.

  本发明涉及对 3-beta-羟基雄甾-4-烯-6,17-二酮（"3-OHAT"）及其代谢物/衍生物在第 3 或 或 碳或 碳或 3 第 和第 17 碳 3-OHAT"）及其代谢物/衍生物的第 6 碳上的甲基、甲氧基、亚甲基、羟甲基或乙酰氧基官能团，以改善和提高哺乳动物的口服生物利用度和/或血浆半衰期和/或药效。
• 1,4,6-androstatriene-3,17-dione ("ATD") for therapeutic uses
  申请人：Kneller W. Bruce

  公开号：US20060154909A1

  公开（公告）日：2006-07-13

  A composition having modified or derivative of 1,4,6-androstatriene-3,17-dione (“ATD”) will improve the health of mammalian subjects. The improvement of health is achieved with the administration of an effective amount of the at least one modified or derivative of 1,4,6-androstatriene-3,17-dione. Particularly, health is improved for a subject suffering with a gynecomastia, and/or estrogen-dependent cancer. Also, subjects recovering from steroid misuse/abuse with treatment in accordance with the present invention. Other improvements found to occur with an administration of ATD is that growth is enhanced and/or stimulated in developing mammals, recovery is shortened in cases of severe trauma or burns, mood levels are improved, male fertility is improved, and athletic performance is improved by increasing testosterone and lean muscle mass.

  一种含有 1,4,6-雄甾三烯-3,17-二酮（"ATD"）改良剂或衍生物的组合物可改善哺乳动物的健康状况。通过服用有效量的至少一种 1,4,6-雄甾三烯-3,17-二酮的改良物或衍生物，可以改善健康状况。特别是对于患有妇科炎症和/或雌激素依赖性癌症的受试者来说，健康状况会得到改善。此外，根据本发明进行治疗后，滥用类固醇的受试者也能恢复健康。施用 ATD 还能改善其他方面，如促进和/或刺激发育中哺乳动物的生长，缩短严重创伤或烧伤病例的恢复期，改善情绪水平，提高男性生育能力，以及通过增加睾酮和瘦肌肉质量提高运动成绩。
• 3β-hydroxyandrost-4-en-6-one derivatives as aromatase inhibitors
  作者：Mitsuteru Numazawa、Ayako Mutsumi、Masachika Tsuji

  DOI：10.1016/0039-128x(89)90004-4

  日期：1989.9

  The 3-formate (II), 3-acetate (III), 3-bromoacetate (IV), 3-propionate (V), 3-methyl ether (VI), and 3-deoxy-derivative (VII) of 3 beta-hydroxyandrost-4-ene-6,17-dione (I) were synthesized and tested in human placental microsomes for their ability to inhibit aromatase. II, III, and VII of this series were potent inhibitors of aromatase with the IC50's (1.7 and 3.3 microM) of the latter two comparable to that (1.2 microM) of 4-hydroxyandrostenedione. Kinetic studies showed that the three steroids are competitive inhibitors of the enzyme with Ki's of 16.0, 5.5, and 0.61 microM for II, III, and VII. Furthermore, II showed a time-dependent, pseudo-first order rate of inactivation of aromatase with Ki of 20.5 microM and kinact of 1.54 x 10(-2) min-1, while III gave a time-dependent, biphasic loss of the enzyme activity. NADPH and oxygen were required for the time-dependent inactivation and the substrate, androstenedione, prevented it.
• Labler,L. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 2226 - 2237
  作者：Labler,L. et al.

  DOI：——

  日期：——
• DE2330582
  申请人：——

  公开号：——

  公开（公告）日：——