3-((E)-hydroximino)-17-(1H-benzimidazol-1-yl)-androsta-4,16-diene | 1382474-97-6

• 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: 3-((E)-hydroximino)-17-(1H-benzimidazol-1-yl)-androsta-4,16-diene
• 英文别名: (10R,13S,E)-17-(1H-benzo[d]imidazol-1-yl)-10,13-dimethyl-1,7,8,9,10,11,12,13,14,15-decahydro-2H-cyclopenta[a]phenanthren-3(6H)-one oxime；(NE)-N-[(8R,9S,10R,13S,14S)-17-(benzimidazol-1-yl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine
• CAS: 1382474-97-6
• 化学式: C₂₆H₃₁N₃O
• 分子量: 401.552
• InChiKey: ACBMPZRTBKJNKP-NWJXPZESSA-N

物化性质

• 沸点：
  599.8±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((E)-hydroximino)-17-(1H-benzimidazol-1-yl)-androsta-4,16-diene 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 (5aR,7aS)-8-(1H-benzo[d]imidazol-1-yl)-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,10,10a,10b,11,12-dodecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one
  参考文献：
  名称：

  [EN] C- 17 -HETEROARYL STEROIDAL COMPOUNDS AS INHIBITORS OF CYP11B, CYP17, AND/OR CYP21
  [FR] INHIBITEURS DE CYP11B, CYP17 ET/OU CYP21

  摘要：

  公开号：

  WO2012083112A3
• 作为产物：
  描述：

  17-(1H-benzimidazol-1-yl)-androsta-4,16-dien-3-one 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-((E)-hydroximino)-17-(1H-benzimidazol-1-yl)-androsta-4,16-diene
  参考文献：
  名称：

  [EN] C- 17 -HETEROARYL STEROIDAL COMPOUNDS AS INHIBITORS OF CYP11B, CYP17, AND/OR CYP21
  [FR] INHIBITEURS DE CYP11B, CYP17 ET/OU CYP21

  摘要：

  公开号：

  WO2012083112A3

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：US20100048912A1

  公开（公告）日：2010-02-25

  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.

  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，包括具有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咪唑或嘧啶并咪唑亲核试剂的亲核乙烯基“加成-消除”取代反应的方法，以及具有钯催化的17-碘雄甾-5,16-二烯-3β-醇或其类似物与三丁基锡二氮杂苯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。
• Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens;Synthesis In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity
  申请人：Brodie Angela

  公开号：US20100048913A1

  公开（公告）日：2010-02-25

  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.

  描述了类固醇C-17苯并咪唑、嘧啶并咪唑（氮杂苯并咪唑）和二氮杂芳烃。还描述了它们的合成方法，其中包括将3β-乙酰氧基-17-氯-16-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将17-碘雄甾-5,16-二烯-3β-醇或其类似物与三丁基锡基二氮杂芳烃进行钯催化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。
• Novel C-17-Heteroaryl Steroidal Cyp17 Inhibitors/Antiandrogens, In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity
  申请人：Brodie Angela

  公开号：US20100048914A1

  公开（公告）日：2010-02-25

  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 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苯并咪唑、嘧啶并咪唑（氮杂苯并咪唑）和二嗪的化合物。还描述了它们的合成方法，包括使用3β-乙酰氧基-17-氯-16-甲酰基-5,16-雌二烯或其类似物和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，以及使用17-碘雄甾-5,16-二烯-3β-醇或其类似物和三丁基锡基二嗪进行钯催化交叉偶联反应的方法。这些化合物是人体CYP 17酶的有效抑制剂，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 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 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。