(3S,10R,13S)-17-Imidazol-1-yl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

• 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: (3S,10R,13S)-17-Imidazol-1-yl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 英文别名: (3S,10R,13S)-17-imidazol-1-yl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₂H₃₀N₂O
• 分子量: 338.5
• InChiKey: PRBTWKCJXZGRAL-XJBINJAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38
• 氢给体数：
  1
• 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：Brodie Angela

  公开号：US20080280864A1

  公开（公告）日：2008-11-13

  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 CYP 17 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.

  描述了类固醇C-17苯并咫唑、嘧啶咪唑咪唑（氮杂苯并咫唑）和二氮杂苯并咪唑。还描述了它们的合成方法，其中包括3β-乙酰氧基-17-氯-16-甲酰基雄甾-5,16-二烯或其类似物和苯并咫唑或嘧啶咪唑亲核试剂的亲核乙烯“加成-消除”取代反应步骤的方法，以及17-碘雄甾-5,16-二烯-3β-醇或其类似物与三丁基锡二氮杂苯基的钯催化交叉偶联反应的方法。这些化合物是人类CYP 17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。这些化合物对于治疗人类前列腺癌是有用的。
• Novel C-17-Heteroaryl Steroidal Cyp17 Inhibitors/Antiandrogens: Synehesis, In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity
  申请人：Brodie Angela

  公开号：US20100137269A1

  公开（公告）日：2010-06-03

  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.

  本文描述了类固醇C-17苯并咪唑，嘧啶并咪唑（氮杂苯并咪唑）和二氮杂苯。还描述了它们的合成方法，其中包括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性乙烯基“加成-消除”取代反应的步骤，以及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。
• NOVEL PRODRUGS OF C-17-HETEROARYL STEROIDAL CYP17 INHIBITORS/ANTIANDROGENS: SYNTHESIS, IN VITRO BIOLOGICAL ACTIVITIES, PHARMACOKINETICS AND ANTITUMOR ACTIVITY
  申请人：Njar Vincent C.O.

  公开号：US20110118219A1

  公开（公告）日：2011-05-19

  Prodrugs of steroidal C-17 benzoazoles, pyrimidinoazoles(azabenzoazoles) 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 prodrug 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 CYP17 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.
• COMPOSITIONS AND METHODS OF INDUCING ENDOPLASMIC RETICULUM STRESS RESPONSE
  申请人：Njar Vincent C.

  公开号：US20110160170A1

  公开（公告）日：2011-06-30

  The present invention provides methods of inducing cell cycle arrest and/or cell growth inhibition, with the methods comprising administering to the cells an effective dose of the compounds of the present invention.
• US20140274983A1
  申请人：——

  公开号：US20140274983A1

  公开（公告）日：2014-09-18