3-(4-aminophenyl)-5-(4-fluorophenyl)-1,2,4-oxadiazole | 96898-87-2

• 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-aminophenyl)-5-(4-fluorophenyl)-1,2,4-oxadiazole
• 英文别名: 4-[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]aniline
• CAS: 96898-87-2
• 化学式: C₁₄H₁₀FN₃O
• 分子量: 255.251
• InChiKey: QDULITXXNYZSMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  64.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异恶唑-5-甲酰氯 、 3-(4-aminophenyl)-5-(4-fluorophenyl)-1,2,4-oxadiazole 在 吡啶 作用下， 以70.4%的产率得到N-{4-[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]phenyl}-1,2-oxazole-5-carboxamide
  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

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.
• 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.