(8R,9S,10R,13S,14S)-16-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione | 929683-50-1

• 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: (8R,9S,10R,13S,14S)-16-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione
• 英文别名: bromo-4-androstene-3,17-dione；16α/β-bromo-4-androstene-3,17-dione；16-bromo-4-androstene-3,17-dione；(8R,9S,10R,13S,14S)-16-bromo-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 929683-50-1
• 化学式: C₁₉H₂₅BrO₂
• 分子量: 365.31
• InChiKey: WSFGMEHHPWEPNC-DTCRIMCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S)-16-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 51.0h， 生成 16β-(imidazol-1-yl)-androsta-1,4-diene-3,17-dione
  参考文献：
  名称：

  具有强大的多种药理特性的新型16-咪唑基取代的甾族衍生物的设计，合成和评估。

  摘要：

  作为我们对一类新型的具有医学活性的16-取代的类固醇的结构-活性关系研究的一部分，在本研究中已合成了几种新的16-咪唑基取代的类固醇衍生物，并进行了药理学评估。新的类固醇类似物5、6、8、9、11和12在源自九种癌症类型的60个癌细胞系中显示出中等的细胞毒性作用。获得了咪唑基取代的甾族衍生物6（DPJ-RG-1241）和7（RB-401）作为芳香化酶的强大抑制剂，其IC50 = 0.18μM和IC50 = 0.168μM，分别比其有效价高约1.2倍和1.4倍到标准药物依西美坦。双季类固醇13和14显示出强效的骨骼肌松弛特性。亲和常数为0。

  DOI：

  10.1016/j.steroids.2012.02.005
• 作为产物：
  描述：

  3β-hydroxy-16α-bromoandrost-5-ene-17-one 在 aluminum isopropoxide 作用下， 以 环己酮 、 甲苯 为溶剂， 反应 1.0h， 以60.33%的产率得到(8R,9S,10R,13S,14S)-16-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione
  参考文献：
  名称：

  NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES

  摘要：

  公开号：

  EP1934241B1

文献信息

• Novel Series of Imidazolyl Substituted Steroidal and Indan-1-One Derivatives
  申请人：Bansal Ranju

  公开号：US20090137541A1

  公开（公告）日：2009-05-28

  The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

  本发明提供了一种新的咪唑基取代类固醇和茚环-1-酮衍生物及其盐，其具有以下一般结构式（A和B）。
• Synthesis, anti-inflammatory and anti-ulcer evaluations of thiazole, thiophene, pyridine and pyran derivatives derived from androstenedione
  作者：Rafat M. Mohareb、Mayssoune Y. Zaki、Nermeen S. Abbas

  DOI：10.1016/j.steroids.2015.03.001

  日期：2015.6

  The reaction of androstenedione with bromine gave the 16-bromo derivative 2. The latter reacted with either cyanothioacetamide or thiourea to give the 2-cyanomethylthiazole derivative 4 and the 2-aminothiazole derivative 13. Compound 4 and 13 were used underwent some condensation, coupling and heterocyclization reactions to give thiophene, pyridine and pyran derivatives. The anti-inflammatory and anti-ulcer evaluations of the newly synthesized products were evaluated and the results showed that 23f showed the maximum antiulcer activity. In addition, toxicity of the most active compounds was studied against shrimp larvae and showed that compounds 2, 23c and 23f showed non-toxicity against the tested organisms. (C) 2015 Elsevier Inc. All rights reserved.