N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methylcarbamoyl-2-nitroaniline | 1372407-00-5

• 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: N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methylcarbamoyl-2-nitroaniline
• 英文别名: 4-(4-cyanoanilino)-2-[4-[(E)-2-cyanoethenyl]-2,6-dimethylphenoxy]-N-methyl-5-nitrobenzamide
• CAS: 1372407-00-5
• 化学式: C₂₆H₂₁N₅O₄
• 分子量: 467.484
• InChiKey: IDKMCGJAGZWQPX-SNAWJCMRSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  631.7±55.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  141.08
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methylcarbamoyl-2-nitroaniline 在 5% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 以65.9%的产率得到5-(4''-cyanoethyl-2'',6''-dimethylphenoxy)-N1-(4'-cyanophenyl)-4-(N-methyl-carbamoyl)-1,2-phenylenediamine
  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：

  5-chloro-N1-(4-cyanophenyl)-4-methoxycarbonyl-2-nitroaniline 在 氯化亚砜 、 potassium tert-butylate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.25h， 生成 N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methylcarbamoyl-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