1-(4-cyanophenyl)-6-[4-[(E)-2-cyanovinyl]-2,6-dimethyl-phenoxy]-N-methyl-benzimidazole-5-carboxamide | 1393736-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(4-cyanophenyl)-6-[4-[(E)-2-cyanovinyl]-2,6-dimethyl-phenoxy]-N-methyl-benzimidazole-5-carboxamide
• 英文别名: 6-[4-[(E)-2-cyanoethenyl]-2,6-dimethylphenoxy]-1-(4-cyanophenyl)-N-methylbenzimidazole-5-carboxamide
• CAS: 1393736-25-8
• 化学式: C₂₇H₂₁N₅O₂
• 分子量: 447.496
• InChiKey: XQCYZRHYHRDZCT-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N1-(4'-cyanophenyl)-5-(4''-(2-cyanovinyl)-2'',6''-dimethylphenoxy)-4-methylcarbamoyl-2-nitroaniline 在 盐酸 、 ammonium hydroxide 、 sodium dithionite 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(4-cyanophenyl)-6-[4-[(E)-2-cyanovinyl]-2,6-dimethyl-phenoxy]-N-methyl-benzimidazole-5-carboxamide
  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