N-tert-butyloxycarbonyl-N'-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-propylsulfamide | 1250438-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-tert-butyloxycarbonyl-N'-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-propylsulfamide
• CAS: 1250438-24-4
• 化学式: C₂₁H₂₆F₃N₅O₅S₂
• 分子量: 549.595
• InChiKey: ZOWNEPGQRMWGNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  131.84
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-N'-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-propylsulfamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到3-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]propylsulfamide
  参考文献：
  名称：

  Structure–activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists

  摘要：

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of hormone refractory prostate cancer. CH4933468 (32d) with a sulfonamide side chain not only exhibited antagonistic activity with no agonistic activity in the reporter gene assay but also inhibited the growth of bicalutamide-resistant cell lines. This compound also inhibited tumor growth of the LNCaP xenograft in mice dose-dependently. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.036
• 作为产物：
  描述：

  4-[3-(3-aminopropyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile 、 N-(叔丁氧基羰基)磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到N-tert-butyloxycarbonyl-N'-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-propylsulfamide
  参考文献：
  名称：

  Structure–activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists

  摘要：

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of hormone refractory prostate cancer. CH4933468 (32d) with a sulfonamide side chain not only exhibited antagonistic activity with no agonistic activity in the reporter gene assay but also inhibited the growth of bicalutamide-resistant cell lines. This compound also inhibited tumor growth of the LNCaP xenograft in mice dose-dependently. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.036