2-(3,4-dimethoxyphenyl)-4,5-dimethyloxazole 3-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,4-dimethoxyphenyl)-4,5-dimethyloxazole 3-oxide
• 英文别名: 2-(3,4-Dimethoxyphenyl)-4,5-dimethyl-3-oxido-1,3-oxazol-3-ium
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: MDLNMKPEFKTBMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-4,5-dimethyloxazole 3-oxide 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以87%的产率得到4-chloromethyl-2-(3,4-dimethoxyphenyl)-5-methyl-1,3-oxazole
  参考文献：
  名称：

  Development of an Aryloxazole Class of Hepatitis C Virus Inhibitors Targeting the Entry Stage of the Viral Replication Cycle

  摘要：

  Reliance on hepatitis C virus (HCV) replicon systems and protein-based screening assays has led to treatments that target HCV viral replication proteins. The model does not encompass other viral replication cycle steps such as entry, processing, assembly and secretion, or viral host factors. We previously applied a phenotypic high-throughput screening platform based on an infectious HCV system and discovered an aryloxazole-based anti-HCV hit. Structure-activity relationship studies revealed several compounds exhibiting EC50 values below 100 nM. Lead compounds showed inhibition of the HCV pseudoparticle entry, suggesting a different mode of action from existing HCV drugs. Hit 7a and lead 7ii both showed synergistic effects in combination with existing HCV drugs. In vivo pharmacokinetics studies of Iii showed high liver distribution and long half-life without obvious hepatotoxicity. The lead compounds are promising as preclinical candidates for the treatment of HCV infection and as molecular probes to study HCV pathogenesis.

  DOI：

  10.1021/acs.jmedchem.7b00561
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 二乙酰一肟 在 盐酸 、 溶剂黄146 作用下， 反应 0.5h， 生成 2-(3,4-dimethoxyphenyl)-4,5-dimethyloxazole 3-oxide
  参考文献：
  名称：

  Preparation of 2-(1-Chloroalkyl)-4,5-dimethyloxazoles and (E)-2-Alkenyl-4,5-dimethyloxazoles

  摘要：

  2-(1-氯烷基)-4,5-二甲基噁唑以84-91%的产率通过POCl3或SOCl2对相应的不稳定N-氧化物进行同时还原和区域选择性氯化制备而成。用氢氧化钾脱氯化的2-(1-氯烷基)-4,5-二甲基噁唑获得(E)-2-烯丙基-4,5-二甲基噁唑，产率为71-90%。

  DOI：

  10.1055/s-2006-942351