4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]aniline | 96898-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]aniline
• 英文别名: 5-(4-aminophenyl)-3-(2-pyridyl)-1,2,4-oxadiazole；3-(pyridin-2-yl)-5-(4-aminophenyl)-1,2,4-oxadiazole；3-(2-pyridyl)-5-(4-aminophenyl)-1,2,4-oxadiazole；4-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)aniline
• CAS: 96898-94-1
• 化学式: C₁₃H₁₀N₄O
• mdl: MFCD09034404
• 分子量: 238.249
• InChiKey: HQHKEUOUVRKITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  邻氯苯甲酰氯 、 4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]aniline 在 吡啶 作用下， 以87%的产率得到2-chloro-N-{4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]phenyl}benzamide
  参考文献：
  名称：

  1,2,4-oxadiazole derivatives as allosteric modulators of metabotropic glutamate receptors belonging to group III

  摘要：

  公开号：

  EP2853532B1
• 作为产物：
  描述：

  2-吡啶基脒肟 在 sodium tetrahydroborate 、 硫化氢 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 为溶剂， 生成 4-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]aniline
  参考文献：
  名称：

  3-Pyridinyl-5-isothiocyanophenyl oxadiazoles

  摘要：

  提供具有以下化学式的化合物，这些化合物可用作驱虫剂、抗真菌剂和抗菌剂。此外，还提供了制备这些化合物的方法、在这些方法中制备的中间体、含有这些化合物的有用组合物以及使用这些化合物和含有相同化合物的组合物的方法。

  公开号：

  US04022901A1

文献信息

• Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
  申请人：——

  公开号：US20030055085A1

  公开（公告）日：2003-03-20

  The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.

  本发明提供了作为代谢型谷氨酸受体拮抗剂的化合物和药物组合物，用于治疗神经系统疾病和障碍。还公开了制备这些化合物的方法。
• 3-Hetero-5-isothiocyanophenyl oxadiazoles as antifungal and
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04065563A1

  公开（公告）日：1977-12-27

  Compounds are provided having the formula ##STR1## which compounds are useful as anthelmintics, and anti-fungal and anti-bacterial agents. In addition, methods for preparing such compounds, intermediates prepared in such methods, useful compositions containing such compounds and methods for employing such compounds and compositions containing the same are also provided.

  提供具有以下化学式的化合物，这些化合物可用作驱虫剂、抗真菌剂和抗菌剂。此外，还提供了制备这些化合物的方法、在这些方法中制备的中间体、含有这些化合物的有用组合物以及使用这些化合物和含有相同化合物的组合物的方法。 ##STR1##
• 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.
• 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.
• US4022901A
  申请人：——

  公开号：US4022901A

  公开（公告）日：1977-05-10