4-{4,4-dimethyl-5-oxo-3-[3-(1H-tetrazol-5-yl)propyl]-2-thioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile | 1233337-56-8

• 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-{4,4-dimethyl-5-oxo-3-[3-(1H-tetrazol-5-yl)propyl]-2-thioxoimidazolidin-1-yl}-2-trifluoromethylbenzonitrile
• 英文别名: 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[3-(2H-tetrazol-5-yl)propyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
• CAS: 1233337-56-8
• 化学式: C₁₇H₁₆F₃N₇OS
• 分子量: 423.422
• InChiKey: LOGXJEFXQHEVPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-(3-{3-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]-propyl}-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 在 三氟乙酸 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以78%的产率得到4-{4,4-dimethyl-5-oxo-3-[3-(1H-tetrazol-5-yl)propyl]-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

• Structure–activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists
  作者：Hitoshi Yoshino、Haruhiko Sato、Kazutaka Tachibana、Takuya Shiraishi、Mitsuaki Nakamura、Masateru Ohta、Nobuyuki Ishikura、Masahiro Nagamuta、Etsuro Onuma、Toshito Nakagawa、Shinichi Arai、Koo-Hyeon Ahn、Kyung-Yun Jung、Hiromitsu Kawata

  DOI：10.1016/j.bmc.2010.03.036

  日期：2010.5

  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.