4-(5-imino-3-{3-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]propyl}-4,4-dimethyl-2-thioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile | 1250438-21-1

• 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-(5-imino-3-{3-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]propyl}-4,4-dimethyl-2-thioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile
• CAS: 1250438-21-1
• 化学式: C₂₅H₂₅F₃N₈OS
• 分子量: 542.588
• InChiKey: WKSXPOLJLSAZJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106.95
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(5-imino-3-{3-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]propyl}-4,4-dimethyl-2-thioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以98%的产率得到4-(3-{3-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]-propyl}-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
• 作为产物：
  描述：

  异丁腈 、 4-甲氧基苄醇 、 4-异硫代氰酰基-2-(三氟甲基)苯甲腈 、 2-[3-(1H-tetrazol-5-yl)propyl]isoindole-1,3-dione 在 三苯基膦 、 偶氮二甲酸二乙酯 、 肼 作用下， 以 二氯甲烷 、 乙醇 、 水 为溶剂， 反应 12.0h， 以26%的产率得到4-(5-imino-3-{3-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]propyl}-4,4-dimethyl-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