2-[1-(4,5,5-Trimethylcyclopenten-1-yl)benzimidazol-2-yl]acetonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[1-(4,5,5-Trimethylcyclopenten-1-yl)benzimidazol-2-yl]acetonitrile
• 英文别名: 2-[1-(4,5,5-trimethylcyclopenten-1-yl)benzimidazol-2-yl]acetonitrile
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.35
• InChiKey: SKXUBXNMGIFPLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

文献信息

• NOVEL C-17-HETEROARYL STEROIDAL CYP17 INHIBITORS/ANTIANDROGENS, IN VITRO BIOLOGICAL ACTIVITIES, PHARMACOKINETICS AND ANTITUMOR ACTIVITY
  申请人：the University of Maryland, Baltimore

  公开号：US20140288036A1

  公开（公告）日：2014-09-25

  Described are steroidal C-17 benzoazoles, pyrimidinoazoles (azabenzoazoles) and diazines. Methods for their synthesis are also described, which include methods having a step of nucleophilic vinylic “addition-elimination” substitution reaction of 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene or analogs thereof and benzoazole or pyrimidinoazole nucleophiles and methods having a palladium catalyzed cross-coupling reaction of 17-iodoandrosta-5,16-dien-3β-ol or analogs thereof with tributylstannyl diazines. The compounds are potent inhibitors of human CYP17 enzyme as well as potent antagonists of both wild type and mutant androgen receptors (AR). The compounds are useful for the treatment of human prostate cancer.

  本文介绍了类固醇C-17苯并咪唑、嘧啶并咪唑（氮杂苯并咪唑）和二氮杂苯的化合物。同时介绍了它们的合成方法，其中包括通过3β-乙酰氧基-17-氯-16-甲酰基雄甾-5，16-二烯或其类似物与苯并咪唑或嘧啶并咪唑亲核试剂进行亲核乙烯基“加成-消除”取代反应的方法，以及通过17-碘雄甾-5，16-二烯-3β-醇或其类似物与三丁基锡基二氮杂苯进行钯催化的交叉偶联反应的方法。这些化合物是人类CYP17酶的有效抑制剂，同时也是野生型和突变雄激素受体（AR）的有效拮抗剂。这些化合物可用于治疗人类前列腺癌。
• US20140274983A1
  申请人：——

  公开号：US20140274983A1

  公开（公告）日：2014-09-18
• NOVEL PRODRUGS OF C-17-HETEROARYL STEROIDAL CYP17 INHIBITORS/ANTIANDROGENS: SYNTHESIS, IN VITRO BIOLOGICAL ACTIVITIES, PHARMACOKINETICS AND ANTITUMOR ACTIVITY
  申请人：University of Maryland, Baltimore

  公开号：US20150174143A1

  公开（公告）日：2015-06-25

  Prodrugs of steroidal C-17 benzoazoles, pyrimidinoazoles (az-abenzoazoles) and diazines. Methods of synthesis are also described, whereby a prodrug group is substituted for a functional group at A ring portion of the ABC ring structure of the steroid. Suitable pro-drug groups include amino acid groups, succinate groups, phosphate groups, or sulfamate groups. The prodrugs of the disclosed compounds allow for improved oral bioavailability of the compounds that are inhibitors of human CYP 17 enzyme as well as potent antagonists of both wild type and mutant androgen receptors (AR). The compounds and the corresponding prodrugs are useful for the treatment of conditions such as human prostate cancer, breast cancer, and prostate hyperplasia.
• US9018198B2
  申请人：——

  公开号：US9018198B2

  公开（公告）日：2015-04-28
• US9295679B2
  申请人：——

  公开号：US9295679B2

  公开（公告）日：2016-03-29