4,5-dimethyl-2-(m-tolyl)oxazole 3-oxide | 913689-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dimethyl-2-(m-tolyl)oxazole 3-oxide
• 英文别名: 4,5-dimethyl-2-m-tolyloxazole 3-oxide；4,5-Dimethyl-2-(3-methylphenyl)-1,3-oxazol-3-ium-3-olate；4,5-dimethyl-2-(3-methylphenyl)-3-oxido-1,3-oxazol-3-ium
• CAS: 913689-60-8
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD15093714
• 分子量: 203.241
• InChiKey: GTMAGMDLEXEBOF-UHFFFAOYSA-N

物化性质

• 沸点：
  358.6±52.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-2-(m-tolyl)oxazole 3-oxide 在 4-二甲氨基吡啶 、 1-羟基苯并三唑一水物 、 potassium hydroxide 、 N,N'-二异丙基碳二亚胺 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 32.5h， 生成 N-(3-(cis-3,5-dimethylpiperidin-1-yl)propyl)-1-((5-methyl-2-(m-tolyl)oxazol-4-yl)methyl)piperidine-4-carboxamide
  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-甲基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 4,5-dimethyl-2-(m-tolyl)oxazole 3-oxide
  参考文献：
  名称：

  ARYLCYCLOAKYL-SUBSTITUTED ALKANOIC ACID DERIVATIVES USEFUL AS PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR (PPAR) LIGANDS FOR THE TREATMENT OF HYPERLIPIDEMIA AND DIABETES

  摘要：

  本发明涉及用于治疗代谢紊乱的化合物和组合物，特别是用于治疗血液中的胰岛素相关代谢紊乱，如高脂血症、糖尿病、胰岛素抵抗等的乙酸衍生物和芳基环烷基取代的烷酸衍生物及其盐。被称为过氧化物酶体增殖物激活受体（PPAR）激动剂/拮抗剂，本发明涉及式I的化合物，其中各种取代基R组在此更具体地定义。

  公开号：

  US20070197605A1

文献信息

• US7598281B2
  申请人：——

  公开号：US7598281B2

  公开（公告）日：2009-10-06
• Development of an Aryloxazole Class of Hepatitis C Virus Inhibitors Targeting the Entry Stage of the Viral Replication Cycle
  作者：Shanshan He、Kelin Li、Billy Lin、Zongyi Hu、Jingbo Xiao、Xin Hu、Amy Q. Wang、Xin Xu、Marc Ferrer、Noel Southall、Wei Zheng、Jeffrey Aubé、Frank J. Schoenen、Juan J. Marugan、T. Jake Liang、Kevin J. Frankowski

  DOI：10.1021/acs.jmedchem.7b00561

  日期：2017.7.27

  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.
• ARYLCYCLOAKYL-SUBSTITUTED ALKANOIC ACID DERIVATIVES USEFUL AS PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR (PPAR) LIGANDS FOR THE TREATMENT OF HYPERLIPIDEMIA AND DIABETES
  申请人：Glombik Heiner

  公开号：US20070197605A1

  公开（公告）日：2007-08-23

  The present invention comprises compounds and compositions for the treatment of metabolic disorders and more particularly, those insulin-related metabolic disorders of the blood such as hyperlipidemia, diabetes, insulin-resistence and the like comprising acetic acid derivatives with arylcycloalkyl-substituted alkanoic acid derivatives and their salts. Known as peroxisome proliferator-activated receptors (PPAR) agonists/antagonists, the invention relates to compounds of the formula I wherein the various substituent R-groups are more specifically defined herein.

  本发明涉及用于治疗代谢紊乱的化合物和组合物，特别是用于治疗血液中的胰岛素相关代谢紊乱，如高脂血症、糖尿病、胰岛素抵抗等的乙酸衍生物和芳基环烷基取代的烷酸衍生物及其盐。被称为过氧化物酶体增殖物激活受体（PPAR）激动剂/拮抗剂，本发明涉及式I的化合物，其中各种取代基R组在此更具体地定义。