17α-20E-21-(4-trifluoromethylphenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol

• 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: 17α-20E-21-(4-trifluoromethylphenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol
• 英文别名: 17α-E-(4-trifluoromethylphenyl)-vinyl estradiol；(8R,9S,13S,14S,17R)-13-methyl-17-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• 化学式: C₂₇H₂₉F₃O₂
• 分子量: 442.521
• InChiKey: TWBFLSYEQYPEAU-LSAOKAHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-碘三氟甲苯 、 炔雌醇 以49%的产率得到17α-20E-21-(4-trifluoromethylphenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol
  参考文献：
  名称：

  合成和评估17alpha-20E-21-（4-取代的苯基）-19-norpregna-1,3,5（10），20-丁烯-3,17beta-二醇作为雌激素受体α激素结合结构域的探针。

  摘要：

  作为开发针对雌激素受体α（ERalpha）的激素结合域的探针的计划的一部分，我们使用溶液和固相Pd（0）催化的组合物，制备了一系列4-对位取代的苯基乙烯基雌二醇衍生物方法。使用从转染的BL21细胞分离的ERα激素结合结构域（HDB）评估化合物5a-j的结合亲和力。结果表明，尽管新化合物的相对结合亲和力（25°C下的RBA为1-60％）比雌二醇（100％）要低一些，但大多数化合物的亲和力都高于未取代的母体苯基乙烯基雌二醇（RBA = 9％）。 。由于取代基并未直接基于理化性质产生构效关系，通过分子建模和分子动力学评估了该系列，以确定配体（尤其是对位取代基）与蛋白质之间的关键相互作用。结果表明，观察到的相对结合亲和力与计算的结合能直接相关，并且并列在对位的氨基酸在结合中起着重要而非主导的作用。总之，我们已经确定17α-E-（4-取代的苯基）乙烯基雌二醇为一类对ERalpha-HBD保持显着亲和

  DOI：

  10.1021/jm0205806

文献信息

• Novel steroidal antiestrogens and antiandrogens and uses thereof
  申请人：——

  公开号：US20040002484A1

  公开（公告）日：2004-01-01

  The present invention comprises the design, synthesis and development of a new class of chemotherapeutic agents for prophylactic and therapeutic treatments in a mammal, particularly a human, believed to be at risk of suffering from a hormone-responsive disorde. In an embodiment of the invention, such treatments include therapeutic compositions comprising novel steroidal antiestrogen and antiandrogen compounds. In a preferred embodiment, such a novel compound of the present invention has an address and a message component, which are made into a single composite entity for more aggressive intervention and effective treatment of hormone-responsive disorders, thereby prolonging the disease-free interval for the patient and reducing a number of side effects.

  本发明涉及设计、合成和开发一类新型化疗药物，用于哺乳动物，特别是人类的预防性和治疗性治疗，被认为处于患有激素敏感性疾病风险中。在本发明的实施例中，这些治疗包括包含新型类固醇抗雌激素和抗雄激素化合物的治疗组合物。在一个首选实施例中，本发明的这种新型化合物具有地址和消息组件，这些组件被制成单个复合实体，用于更积极地干预和有效治疗激素敏感性疾病，从而延长患者的无病间隔时间并减少副作用数量。
• [EN] NOVEL STEROIDAL ANTIESTROGENS AND ANTIANDROGENS AND USES THEREOF<br/>[FR] NOUVEAUX ANTIOESTROGENES ET ANTIANDROGENES STEROIDIENS ET UTILISATIONS DE CEUX-CI
  申请人：UNIV NORTHEASTERN

  公开号：WO2001098322A1

  公开（公告）日：2001-12-27

  The present invention comprises the design, synthesis and development of a new class of chemotherapeutic agents for prophylactic and therapeutic treatments in a mammal, particularly a human, believed to be at risk of suffering from a hormone-responsive disorde. In an embodiment of the invention, such treatments include therapeutic compositions comprising novel steroidal antiestrogen and antiandrogen compounds. In a preferred embodiment, such a novel compound of the present invention has an address and a message component, which are made into a single composite entity for more aggressive intervention and effective treatment of hormone-responsive disorders, thereby prolonging the disease-free interval for the patient and reducing a number of side effects.

  本发明涉及一种新的化疗药物的设计、合成和开发，用于哺乳动物，特别是人类，被认为有患荷尔蒙反应性疾病的风险的预防和治疗。在本发明的实施例中，这种治疗包括含有新型类固醇抗雌激素和抗雄激素化合物的治疗组合物。在本发明的优选实施例中，这种新型化合物具有地址和信息组件，这些组件组成单一的复合实体，以更积极的干预和有效治疗荷尔蒙反应性疾病，从而延长患者的无病时间并减少副作用的数量。
• Solid Phase Synthesis of 17α-E/Z-(X-Phenyl)-Vinyl Estradiols Using the Stille Coupling Reaction
  作者：Choon Young Lee、Robert N Hanson

  DOI：10.1016/s0040-4020(00)00004-1

  日期：2000.3
• Steroidal antiestrogens and antiandrogens and uses thereof
  申请人：Hanson Robert N.

  公开号：US20080166301A1

  公开（公告）日：2008-07-10

  The present invention comprises the design, synthesis and development of a new class of chemotherapeutic agents for prophylactic and therapeutic treatments in a mammal, particularly a human, believed to be at risk of suffering from a hormone-responsive disorder. In an aspect of the invention, such treatments include therapeutic compositions comprising novel steroidal antiestrogen and antiandrogen compounds. In a preferred aspect, such a novel compound of the present invention has an address and a message component, which are made into a single composite entity for more aggressive intervention and effective treatment of hormone-responsive disorders, thereby prolonging the disease-free interval for the patient and reducing a number of side effects.
• US7041839B2
  申请人：——

  公开号：US7041839B2

  公开（公告）日：2006-05-09