4-{4-(4-nitrobenzoylamino)phenoxy}phenol | 76960-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{4-(4-nitrobenzoylamino)phenoxy}phenol
• 英文别名: N-[4-(4-hydroxyphenoxy)phenyl]-4-nitrobenzamide
• CAS: 76960-35-5
• 化学式: C₁₉H₁₄N₂O₅
• 分子量: 350.331
• InChiKey: HCBNELUSHGGTMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-硝基苯氧基)苯酚 在 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 4-{4-(4-nitrobenzoylamino)phenoxy}phenol
  参考文献：
  名称：

  Design and Synthesis of 4-(4-Benzoylaminophenoxy)phenol Derivatives As Androgen Receptor Antagonists

  摘要：

  We report the design and synthesis of novel 4-(4-benzoylaminophenoxy)phenol derivatives that bind to the androgen receptor (AR) ligand-binding domain and exhibit potent androgen-antagonistic activity. Compound 22 is one of the most potent of these derivatives, inhibiting the dihydrotestosterone-promoted growth of SC-3 cell line bearing wild-type AR (IC50 0.75 mu M), LNCaP cell line bearing T877A-mutated AR (IC50 0.043 mu M), and 22Rv1 cell line bearing H874Y-mutated AR (IC50 0.22 mu M). Structure activity relationship studies confirmed that the pharmacophore of these novel AR antagonists is distinct from the nitro- or cyano-substituted anilide substructure of other nonsteroidal AR antagonists. This novel pharmacophore is expected to provide a basis for designing new antiprostate cancer agents.

  DOI：

  10.1021/ml4001744

文献信息

• An unusual nucleophilic attack on a carbonyl oxygen. Reaction of a positively charged oxygen atom
  作者：Koichi Shudo、Yutaka Orihara、Toshiharu Ohta、Toshihiko Okamoto

  DOI：10.1021/ja00394a040

  日期：1981.2
• SCHUDO KOICHI; ORIHARA YUTAKA; OHTA TOSHIHARU; OKAMOTO TOSHIHIKO, J. AMER. CHEM. SOC., 1981, 103, NO 4, 943-944
  作者：SCHUDO KOICHI、 ORIHARA YUTAKA、 OHTA TOSHIHARU、 OKAMOTO TOSHIHIKO

  DOI：——

  日期：——
• Design and Synthesis of 4-(4-Benzoylaminophenoxy)phenol Derivatives As Androgen Receptor Antagonists
  作者：Ayumi Yamada、Shinya Fujii、Shuichi Mori、Hiroyuki Kagechika

  DOI：10.1021/ml4001744

  日期：2013.10.10

  We report the design and synthesis of novel 4-(4-benzoylaminophenoxy)phenol derivatives that bind to the androgen receptor (AR) ligand-binding domain and exhibit potent androgen-antagonistic activity. Compound 22 is one of the most potent of these derivatives, inhibiting the dihydrotestosterone-promoted growth of SC-3 cell line bearing wild-type AR (IC50 0.75 mu M), LNCaP cell line bearing T877A-mutated AR (IC50 0.043 mu M), and 22Rv1 cell line bearing H874Y-mutated AR (IC50 0.22 mu M). Structure activity relationship studies confirmed that the pharmacophore of these novel AR antagonists is distinct from the nitro- or cyano-substituted anilide substructure of other nonsteroidal AR antagonists. This novel pharmacophore is expected to provide a basis for designing new antiprostate cancer agents.