3-(4-methoxyphenyl)-5-methylthio-1,2,4-oxadiazole | 1419180-26-9

• 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-methoxyphenyl)-5-methylthio-1,2,4-oxadiazole
• 英文别名: 3-(4-Methoxyphenyl)-5-methylsulfanyl-1,2,4-oxadiazole；3-(4-methoxyphenyl)-5-methylsulfanyl-1,2,4-oxadiazole
• CAS: 1419180-26-9
• 化学式: C₁₀H₁₀N₂O₂S
• 分子量: 222.268
• InChiKey: AYDUXJOVYAUUGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ALPHA-氯-4-甲氧基苯甲醛肟 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 52.0h， 生成 3-(4-methoxyphenyl)-5-methylthio-1,2,4-oxadiazole
  参考文献：
  名称：

  1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents

  摘要：

  1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1-azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.007

文献信息

• [EN] SUBSTITUTED 1,2,4-OXADIAZOLE, ITS APPLICATION AND A PHARMACEUTICAL PREPARATION COMPRISING IT<br/>[FR] 1,2,4-OXADIAZOLE SUBSTITUÉ, SON APPLICATION ET PRÉPARATION PHARMACEUTIQUE LE COMPRENANT
  申请人：SVENOX PHARMACEUTICALS LLC

  公开号：WO2020128675A1

  公开（公告）日：2020-06-25

  Substances effective against tuberculosis based on substituted 1,2,4-oxadiazoles of general formula I, where Y = S or CH2 and R = phenyl- or phenyl- substituted in positions 2, 3, 4, and 5 by one or several electron-acceptor groups or electron-donor groups. These compounds can be produced by easy syntheses and are characterized by low toxicity and high efficacy against mycobacteria, including multiresistant strains thereof. The invention also discloses a pharmaceutical preparation containing substituted 1,2,4-oxadiazole of formula I as active substance as well as the use of this substituted 1,2,4-oxadiazole as an antituberculosis drug.

  基于通式I的取代1,2,4-噁二唑，其中Y = S或CH2，R = 苯基或在2,3,4和5位上被一个或多个电子受体基团或电子给体基团取代的苯基。这些化合物可以通过简单的合成方法制备，并具有低毒性和高效抗结核分枝杆菌的特性，包括多重耐药菌株。本发明还揭示了一种含有通式I的取代1,2,4-噁二唑作为活性物质的药物制剂，以及将这种取代1,2,4-噁二唑用作抗结核药物的用途。