N1-(4'-cyanophenyl)-5-(2'',6''-dimethyl-4''-(3-oxobut-1-enyl)phenoxy)-4-trifluoromethyl-2-nitroaniline | 1393736-02-1

• 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: N1-(4'-cyanophenyl)-5-(2'',6''-dimethyl-4''-(3-oxobut-1-enyl)phenoxy)-4-trifluoromethyl-2-nitroaniline
• 英文别名: 4-[5-[2,6-dimethyl-4-[(E)-3-oxobut-1-enyl]phenoxy]-2-nitro-4-(trifluoromethyl)anilino]benzonitrile
• CAS: 1393736-02-1
• 化学式: C₂₆H₂₀F₃N₃O₄
• 分子量: 495.458
• InChiKey: MLIUBZIIORSUDP-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N1-(4'-cyanophenyl)-5-(2'',6''-dimethyl-4''-(3-oxobut-1-enyl)phenoxy)-4-trifluoromethyl-2-nitroaniline 在 5% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 以50%的产率得到4-[2-Amino-5-[2,6-dimethyl-4-(3-oxobutyl)phenoxy]-4-(trifluoromethyl)anilino]benzonitrile
  参考文献：
  名称：

  Design, Synthesis, and Preclinical Evaluations of Novel 4-Substituted 1,5-Diarylanilines as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor (NNRTI) Drug Candidates

  摘要：

  Twenty-one new 4-substituted diarylaniline compounds (DAANs) (series 13, 14, and 15) were designed, synthesized, and evaluated against wildtype and drug resistant HIV-1 viral strains. As a result, approximately a dozen new DAANs showed high potency with low nano- to subnanomolar EC50 values ranging from 0.2 to 10 nM. The three most promising compounds 14e, 14h, and 15h exhibited high potency against wild-type and drug-resistant viral strains with EC50 values at the subnanomolar level (0.29-0.87 nM) and were comparable to or more potent than the new NNRTI drug riplivirine (2) in the same assays. Drug like physicochemical property assessments revealed that the most active DAANs (EC50 < 10 nM) have better aqueous solubility (>1-90 mu g/mL at pH 7.4 and pH 2) and metabolic stability in vitro than 2, as well as desirable log P values (<5) and polar surface areas (PSA) (<140 A(2)). These promising results warrant further development of this novel compound class as potential potent anti-AIDS clinical trial candidates.

  DOI：

  10.1021/jm3007678
• 作为产物：
  描述：

  2,4-二氯-5-硝基三氟甲基苯 在 potassium tert-butylate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.42h， 生成 N1-(4'-cyanophenyl)-5-(2'',6''-dimethyl-4''-(3-oxobut-1-enyl)phenoxy)-4-trifluoromethyl-2-nitroaniline
  参考文献：
  名称：

  Design, Synthesis, and Preclinical Evaluations of Novel 4-Substituted 1,5-Diarylanilines as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor (NNRTI) Drug Candidates

  摘要：

  Twenty-one new 4-substituted diarylaniline compounds (DAANs) (series 13, 14, and 15) were designed, synthesized, and evaluated against wildtype and drug resistant HIV-1 viral strains. As a result, approximately a dozen new DAANs showed high potency with low nano- to subnanomolar EC50 values ranging from 0.2 to 10 nM. The three most promising compounds 14e, 14h, and 15h exhibited high potency against wild-type and drug-resistant viral strains with EC50 values at the subnanomolar level (0.29-0.87 nM) and were comparable to or more potent than the new NNRTI drug riplivirine (2) in the same assays. Drug like physicochemical property assessments revealed that the most active DAANs (EC50 < 10 nM) have better aqueous solubility (>1-90 mu g/mL at pH 7.4 and pH 2) and metabolic stability in vitro than 2, as well as desirable log P values (<5) and polar surface areas (PSA) (<140 A(2)). These promising results warrant further development of this novel compound class as potential potent anti-AIDS clinical trial candidates.

  DOI：

  10.1021/jm3007678