4-[3-(3-aminopropyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile | 1233337-49-9

• 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: 4-[3-(3-aminopropyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile
• 英文别名: 4-[3-(3-Aminopropyl)-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
• CAS: 1233337-49-9
• 化学式: C₁₆H₁₇F₃N₄OS
• 分子量: 370.398
• InChiKey: BATZNWUPUQWGQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-{3-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile 在 肼 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 以62%的产率得到4-[3-(3-aminopropyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile
  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

文献信息

• Diarylhydantoin Compounds
  申请人：The Regents of the University of California

  公开号：US20180086718A1

  公开（公告）日：2018-03-29

  The present invention relates to diarylhydantoin compounds, including diarylthiohydantoins, and methods for synthesizing them and using them in the treatment of hormone refractory prostate cancer.