5-(2-氯苯基)-3-(4-硝基苯基)-1,2,4-噁二唑 | 861238-44-0

• 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-氯苯基)-3-(4-硝基苯基)-1,2,4-噁二唑
• 中文别名: 5-(2-氯苯基)-3-(4-硝基苯基)-1,2,4-恶二唑
• 英文名称: 5-(2-chlorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
• CAS: 861238-44-0
• 化学式: C₁₄H₈ClN₃O₃
• 分子量: 301.689
• InChiKey: VAJPOGWNCSNRAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 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：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  对硝基苯甲腈 在 盐酸羟胺 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 0.17h， 生成 5-(2-氯苯基)-3-(4-硝基苯基)-1,2,4-噁二唑
  参考文献：
  名称：

  New 1,2,4-oxadiazole derivatives with positive mGlu₄ receptor modulation activity and antipsychotic-like properties

  摘要：

  Considering the allosteric regulation of mGlu receptors for potential therapeutic applications, we developed a group of 1,2,4-oxadiazole derivatives that displayed mGlu4 receptor positive allosteric modulatory activity (EC50 = 282-656 nM). Selectivity screening revealed that they were devoid of activity at mGlu1, mGlu2 and mGlu5 receptors, but modulated mGlu7 and mGlu8 receptors, thus were classified as group III-preferring mGlu receptor agents. None of the compounds was active towards hERG channels or in the mini-AMES test. The most potent in vitro mGlu4 PAM derivative 52 (N-(3-chloro-4-(5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl)phenyl)picolinamide) was readily absorbed after i.p. administration (male Albino Swiss mice) and reached a maximum brain concentration of 949.76 ng/mL. Five modulators (34, 37, 52, 60 and 62) demonstrated significant anxiolytic- and antipsychotic-like properties in the SIH and DOI-induced head twitch test, respectively. Promising data were obtained, especially for N-(4-(5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)picolinamide (62), whose effects in the DOI-induced head twitch test were comparable to those of clozapine and better than those reported for the selective mGlu4 PAM ADX88178.

  DOI：

  10.1080/14756366.2021.1998022

文献信息

• 1,2,4-oxadiazole derivatives as allosteric modulators of metabotropic glutamate receptors belonging to group III
  申请人：Instytut Farmakologii Polskiej Akademii Nauk

  公开号：EP2853532B1

  公开（公告）日：2020-12-09