O-4-cyanonaphthalen-1-yl dimethylcarbamothioate | 1309391-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: O-4-cyanonaphthalen-1-yl dimethylcarbamothioate
• 英文别名: O-(4-cyanonaphthalen-1-yl) N,N-dimethylcarbamothioate
• CAS: 1309391-74-9
• 化学式: C₁₄H₁₂N₂OS
• 分子量: 256.328
• InChiKey: KFCJEYRULBUIQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-4-cyanonaphthalen-1-yl dimethylcarbamothioate 在 甲醇 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 4-mercapto-1-naphthonitrile
  参考文献：
  名称：

  Unexpected Binding Orientation of Bulky-B-Ring Anti-Androgens and Implications for Future Drug Targets

  摘要：

  Several new androgen receptor antagonists were synthesized and found to have varying activities across typically antiandrogen resistant mutants (Thr877 -> Ala and Trp741 -> Leu) and markedly improved potency over previously reported pan-antagonists. X-ray crystallography of a new anti-androgen in an androgen receptor mutant (Thr877 -> Ala) shows that the receptor can accommodate the added bulk presented by phenyl to naphthyl substitution, casting doubt on previous reports of predicted binding orientation and the causes of antagonism in bulky-B-ring antagonists.

  DOI：

  10.1021/jm2000097
• 作为产物：
  描述：

  4-羟基萘-1-甲腈 、 二甲氨基硫代甲酰氯 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 O-4-cyanonaphthalen-1-yl dimethylcarbamothioate
  参考文献：
  名称：

  Unexpected Binding Orientation of Bulky-B-Ring Anti-Androgens and Implications for Future Drug Targets

  摘要：

  Several new androgen receptor antagonists were synthesized and found to have varying activities across typically antiandrogen resistant mutants (Thr877 -> Ala and Trp741 -> Leu) and markedly improved potency over previously reported pan-antagonists. X-ray crystallography of a new anti-androgen in an androgen receptor mutant (Thr877 -> Ala) shows that the receptor can accommodate the added bulk presented by phenyl to naphthyl substitution, casting doubt on previous reports of predicted binding orientation and the causes of antagonism in bulky-B-ring antagonists.

  DOI：

  10.1021/jm2000097

文献信息

• Unexpected Binding Orientation of Bulky-B-Ring Anti-Androgens and Implications for Future Drug Targets
  作者：Charles B. Duke、Amanda Jones、Casey E. Bohl、James T. Dalton、Duane D. Miller

  DOI：10.1021/jm2000097

  日期：2011.6.9

  Several new androgen receptor antagonists were synthesized and found to have varying activities across typically antiandrogen resistant mutants (Thr877 -> Ala and Trp741 -> Leu) and markedly improved potency over previously reported pan-antagonists. X-ray crystallography of a new anti-androgen in an androgen receptor mutant (Thr877 -> Ala) shows that the receptor can accommodate the added bulk presented by phenyl to naphthyl substitution, casting doubt on previous reports of predicted binding orientation and the causes of antagonism in bulky-B-ring antagonists.