5-(4-fluorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole | 96898-35-0

• 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-(4-fluorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
• CAS: 96898-35-0
• 化学式: C₁₄H₈FN₃O₃
• 分子量: 285.234
• InChiKey: JEYGGQFIDFVSGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  6

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-(4-fluorophenyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
  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
• Antiparasitic agents. 6. Synthesis and anthelmintic activities of novel isothiocyanatophenyl-1,2,4-oxadiazoles
  作者：R. D. Haugwitz、A. J. Martinez、J. Venslavsky、R. G. Angel、B. V. Maurer、G. A. Jacobs、V. L. Narayanan、L. R. Cruthers、J. Szanto

  DOI：10.1021/jm00147a019

  日期：1985.9

  The syntheses and anthelmintic activities of 31 3- and 5-(isothiocyanatophenyl)-1,2,4-oxadiazoles are reported. In the primary anthelmintic screen, 3-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (39) showed 100% nematocidal activity and 3-(2-furanyl)-5-(4-isothiocyanatophenyl)-1,2,4-oxadiazole (63), 3-(2-furanyl)-5-(2-chloro-4-isothiocyanatophenyl)-1,2,4-oxadiazole (64), and 3-(2-furanyl)-5-(4-chloro-3-isothiocyanatophenyl)-1,2,4-oxadiazole (66) showed 100% taeniacidal activity when administered orally to mice. The two most active members of this series, 39 and 63, were active against the gastrointestinal nematodes of sheep at 100 mg/kg. In addition, 39 was also found to be active against hookworms in dogs at a single, oral dose of 200 mg/kg.
• Microwave assisted synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from substituted amidoximes and benzoyl cyanides
  作者：Shivaji Kandre、Pundlik Rambhau Bhagat、Rajiv Sharma、Amol Gupte

  DOI：10.1016/j.tetlet.2013.04.101

  日期：2013.7

  We report herein the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from amidoximes and substituted or unsubstituted benzoyl cyanides under microwave irradiation. Substituted or unsubstituted O-carboxyphenyl amidoxime is a key intermediate of this alternative method developed for the synthesis of these heterocycles. These reactions employ simple synthetic protocols devoid of lengthy purification procedures and proceed with good yield. (c) 2013 Elsevier Ltd. All rights reserved.
• New 1,2,4-oxadiazole derivatives with positive mGlu₄ receptor modulation activity and antipsychotic-like properties
  作者：Anna Stankiewicz、Katarzyna Kaczorowska、Ryszard Bugno、Aneta Kozioł、Maria H. Paluchowska、Grzegorz Burnat、Barbara Chruścicka、Paulina Chorobik、Piotr Brański、Joanna M. Wierońska、Beata Duszyńska、Andrzej Pilc、Andrzej J. Bojarski

  DOI：10.1080/14756366.2021.1998022

  日期：2022.12.31

  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.