5-(2-甲基苯基)-3-(3-甲基苯基)-1,2,4-恶二唑 | 651032-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(2-甲基苯基)-3-(3-甲基苯基)-1,2,4-恶二唑
• 英文名称: 3-(3-toluyl)-5-(2-toluyl)-1,2,4-oxadiazole
• 英文别名: 5-(2-Methylphenyl)-3-(3-methylphenyl)-1,2,4-oxadiazole
• CAS: 651032-75-6
• 化学式: C₁₆H₁₄N₂O
• mdl: MFCD03720899
• 分子量: 250.3
• InChiKey: PEUKZLZAZRXGAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基苄胺肟 、 邻甲基苯甲酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 以92%的产率得到5-(2-甲基苯基)-3-(3-甲基苯基)-1,2,4-恶二唑
  参考文献：
  名称：

  Exploring the readthrough of nonsense mutations by non-acidic Ataluren analogues selected by ligand-based virtual screening

  摘要：

  Ataluren, also known as PTC124, is a 5-(fluorophenyI)-1,2,4-oxadiazolyl-benzoic acid suggested to suppress nonsense mutations by readthrough of premature stop codons in the mRNA. Potential interaction of PTC124 with mRNA has been recently studied by molecular dynamics simulations highlighting the importance of H-bonding and stacking pi-pi interactions. A series of non-acidic analogues of PTC124 were selected from a large database via a ligand-based virtual screening approach. Eight of them were synthesized and tested for their readthrough activity using the Fluc reporter harboring the UGA premature stop codon. The most active compound was further tested for suppression of the UGA nonsense mutation in the bronchial epithelial IB3.1 cell line carrying the W1282X mutation in the CFTR gene. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.06.048

文献信息

• The accelerated development of an optimized synthesis of 1,2,4-oxadiazoles: application of microwave irradiation and statistical design of experiments
  作者：Marc D Evans、Jessica Ring、Adam Schoen、Andrew Bell、Paul Edwards、Didier Berthelot、Robb Nicewonger、Carmen M Baldino

  DOI：10.1016/j.tetlet.2003.10.055

  日期：2003.12

  Herein, we report the development of an optimized microwave-assisted synthesis of 1,2,4-oxadiazoles. The chemistry development process was significantly accelerated by employing a statistical software package (MODDE 6.0(TM)) to guide in the optimization of the reaction conditions. The resulting optimized reaction conditions were then utilized in the synthesis of a focused library of 1,2,4-oxadiazoles. (C) 2003 Published by Elsevier Ltd.