3-(4′-pyridyl)-5-(3′-toluyl)-1,2,4-oxadiazole | 88059-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4′-pyridyl)-5-(3′-toluyl)-1,2,4-oxadiazole
• 英文别名: 5-(3-methylphenyl)-3-(4-pyridyl)-1,2,4-oxadiazole；3-(4-pyridyl)-5-(3-toluyl)-1,2,4-oxadiazole；4-(5-m-Tolyl-[1,2,4]oxadiazol-3-yl)-pyridine；5-(3-methylphenyl)-3-pyridin-4-yl-1,2,4-oxadiazole
• CAS: 88059-54-5
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: IBTAWSWYHNVHJW-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C(Solv: acetone (67-64-1); water (7732-18-5))
• 沸点：
  432.7±55.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)
• 溶解度：
  3.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-Methyl-N-pyridin-4-ylmethyl-benzamide 在 亚硝酰氯 作用下， 以 氯仿 为溶剂， 以16%的产率得到3-(4′-pyridyl)-5-(3′-toluyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  5-芳基-3-（4-吡啶基）-1,2,4-恶二唑的合成

  摘要：

  在N-（4-吡啶基甲基）芳基酰胺与亚硝酰氯的反应中以低收率形成标题恶二唑。

  DOI：

  10.1002/jhet.5570200548

文献信息

• Exploring the readthrough of nonsense mutations by non-acidic Ataluren analogues selected by ligand-based virtual screening
  作者：Ivana Pibiri、Laura Lentini、Marco Tutone、Raffaella Melfi、Andrea Pace、Aldo Di Leonardo

  DOI：10.1016/j.ejmech.2016.06.048

  日期：2016.10

  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.
• 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.
• BRANA, M. F.;CASTELLANO, J. M.;YUNTA, M. J. R., J. HETEROCYCL. CHEM., 1983, 20, N 5, 1403-1405
  作者：BRANA, M. F.、CASTELLANO, J. M.、YUNTA, M. J. R.

  DOI：——

  日期：——