N,N-dibenzyl-6-bromopyridine-2-sulfonamide | 1043446-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N-dibenzyl-6-bromopyridine-2-sulfonamide
• 英文别名: 6-bromopyridine-2-sulfonic acid dibenzylamide
• CAS: 1043446-50-9
• 化学式: C₁₉H₁₇BrN₂O₂S
• 分子量: 417.326
• InChiKey: QUKMNYNAOPFLGR-UHFFFAOYSA-N

物化性质

• 沸点：
  575.5±60.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-6-bromopyridine-2-sulfonamide 在 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三甲基硅烷化重氮甲烷 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 methyl 1-((6-(N,N-dibenzylsulfamoyl)pyridin-2-yl)amino)cyclobutanecarboxylate
  参考文献：
  名称：

  [EN] SUBSTITUTED THIOHYDANTOIN DERIVATIVES AS ANDROGEN RECEPTOR ANTAGONISTS
  [FR] UTILISATION DE DÉRIVÉS DE THIOHYDANTOIN SUBSTITUÉ EN TANT QU'ANTAGONISTES DES RÉCEPTEURS D'ANDROGÈNES

  摘要：

  揭示了用于治疗受到一个或多个雄激素受体拮抗影响的疾病的化合物、组合物和方法。这些化合物由以下的化学式（I）表示：化学式（I）其中R1和G在此处定义。

  公开号：

  WO2017123542A1
• 作为产物：
  描述：

  二苄胺 、 6-溴吡啶-2-磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以2.17 g的产率得到N,N-dibenzyl-6-bromopyridine-2-sulfonamide
  参考文献：
  名称：

  Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer

  摘要：

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem with agonist metabolites, novel thiohydantoin derivatives were identified by applying two strategies. One was the replacement of the alkylsulfonamide moiety by a phenylsulfonamide to avoid the production of agonist metabolites. The other was the replacement of the phenyl ring with a pyridine ring to improve in vivo potency and reduce hERG affinity. Pharmacological assays indicated that CH5137291 (17b) was a potent AR pure antagonist which did not produce the agonist metabolite. Moreover, CH5137291 completely inhibited in vivo tumor growth of LNCaP-BC2, a castration-resistant prostate cancer model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.023

文献信息

• Cyclic Urea Derivatives As Androgen Receptor Antagonists
  申请人：Bock Mark Gary

  公开号：US20140329858A1

  公开（公告）日：2014-11-06

  The present invention is directed to compounds of formula (I) wherein R 1 , R 2 , R 3 , and A are defined herein. The present invention also provides for pharmaceutical compositions comprising a compound of formula (I) as well as to the use of such compounds as androgen receptor antagonists for the treatment of diseases and conditions mediated by the androgen receptor, such as prostate cancer.

  本发明涉及式（I）中R1、R2、R3和A所定义的化合物。本发明还提供了包含式（I）化合物的药物组合物，以及将这些化合物用作雄激素受体拮抗剂治疗由雄激素受体介导的疾病和症状，如前列腺癌。
• Substituted thiohydantoin derivatives as androgen receptor antagonists
  申请人：Janssen Pharmaceutica NV

  公开号：US10000502B2

  公开（公告）日：2018-06-19

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the antagonism of one or more androgen receptor types. Such compounds are represented by Formula (I) as follows: wherein R1 and G are defined herein.

  公开了用于治疗受一种或多种雄激素受体类型拮抗作用影响的疾病的化合物、组合物和方法。此类化合物由如下式（I）表示： 其中 R1 和 G 在此定义。
• SUBSTITUTED THIOHYDANTOIN DERIVATIVES AS ANDROGEN RECEPTOR ANTAGONISTS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP3402791A1

  公开（公告）日：2018-11-21
• Substituted Thiohydantoin Derivatives As Androgen Receptor Antagonists
  申请人：Janssen Pharmaceutica NV

  公开号：US20180298021A1

  公开（公告）日：2018-10-18

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the antagonism of one or more androgen receptor types. Such compounds are represented by Formula (I) as follows: wherein R 1 and G are defined herein.