5-(2,4-dichlorophenyl)-3-(pyridin-4-yl)-1,2,4-oxadiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,4-dichlorophenyl)-3-(pyridin-4-yl)-1,2,4-oxadiazole
• 英文别名: 4-[5-(2,4-Dichlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine；5-(2,4-dichlorophenyl)-3-pyridin-4-yl-1,2,4-oxadiazole
• 化学式: C₁₃H₇Cl₂N₃O
• 分子量: 292.124
• InChiKey: XQNVKVJVJOHLED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,4-二氯苯甲酸 、 4-吡啶基偕胺肟 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 生成 5-(2,4-dichlorophenyl)-3-(pyridin-4-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  The accelerated development of an optimized synthesis of 1,2,4-oxadiazoles: application of microwave irradiation and statistical design of experiments

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2003.10.055

文献信息

• Bis-aryloxadiazoles as effective activators of the aryl hydrocarbon receptor
  作者：Kaitlin J. Basham、Vasudev R. Bhonde、Collin Kieffer、James B.C. Mack、Matthew Hess、Bryan E. Welm、Ryan E. Looper

  DOI：10.1016/j.bmcl.2014.04.013

  日期：2014.6

  Bis-aryloxadiazoles are common scaffolds in medicinal chemistry due to their wide range of biological activities. Previously, we identified a 1,2,4-bis-aryloxadiazole that blocks mammary branching morphogenesis through activation of the aryl hydrocarbon receptor (AHR). In addition to defects in mammary differentiation, AHR stimulation induces toxicity in many other tissues. We performed a structure activity relationship (SAR) study of 1,2,4-bis-aryloxadiazole to determine which moieties of the molecule are critical for AHR activation. We validated our results with a functional biological assay, using desmosome formation during mammary morphogenesis to indicate AHR activity. These findings will aid the design of oxadiazole derivative therapeutics with reduced off-target toxicity profiles. (C) 2014 Elsevier Ltd. 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.