4-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid | 883541-64-8

• 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-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid
• CAS: 883541-64-8
• 化学式: C₁₂H₁₁FN₂O₃
• mdl: MFCD08133364
• 分子量: 250.229
• InChiKey: ADZWCBJOLPWMPT-UHFFFAOYSA-N

物化性质

• 沸点：
  446.3±55.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  4-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 diethylaminodifluorosulfinium tetrafluoroborate 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 N-[9-(2-Fluoroethyl)-9H-carbazol-3-yl]-4-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]butanamide
  参考文献：
  名称：

  Development of fluorinated CB2 receptor agonists for PET studies

  摘要：

  A convergent strategy was followed to modify systematically carbazole based CB2 receptor ligands. The length of the N-(fluoroalkyl) group (n in 7), the length of the alkanamide (m in 7) and the substitution pattern of the phenyl moiety (X and Y in 7) were varied systematically. The highest CB2 affinity was found for the 2-fluoroethyl substituted carbazole derivative 20a (K-i = 5.8 nM) containing the propionamide and the 2-bromo-4-fluorophenyl moiety. According to docking studies 20a fits nicely into the binding pocket of the CB2 receptor, but elongation of the fluoroethyl side chain leads to a different binding mode of the ligands. The high CB2 affinity together with the high selectivity over the CB2 subtype qualifies the fluoroethyl derivative 20a to be developed as a PET tracer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.040
• 作为产物：
  描述：

  戊二酸酐 、 对氟苯腈 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以56%的产率得到4-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid
  参考文献：
  名称：

  Development of fluorinated CB2 receptor agonists for PET studies

  摘要：

  A convergent strategy was followed to modify systematically carbazole based CB2 receptor ligands. The length of the N-(fluoroalkyl) group (n in 7), the length of the alkanamide (m in 7) and the substitution pattern of the phenyl moiety (X and Y in 7) were varied systematically. The highest CB2 affinity was found for the 2-fluoroethyl substituted carbazole derivative 20a (K-i = 5.8 nM) containing the propionamide and the 2-bromo-4-fluorophenyl moiety. According to docking studies 20a fits nicely into the binding pocket of the CB2 receptor, but elongation of the fluoroethyl side chain leads to a different binding mode of the ligands. The high CB2 affinity together with the high selectivity over the CB2 subtype qualifies the fluoroethyl derivative 20a to be developed as a PET tracer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.040

文献信息

• A second generation of 1,2,4-oxadiazole derivatives with enhanced solubility for inhibition of 3-hydroxykynurenine transaminase (HKT) from <i>Aedes aegypti</i>
  作者：Larissa G. Maciel、Andrey da S. Barbosa、Edilson B. de Alencar-Filho、Thereza A. Soares、Janaína V. dos Anjos

  DOI：10.1039/d0md00305k

  日期：——

  (HKT). Previously, we have reported the effectiveness of 1,2,4-oxadiazole derivatives acting as larvicides for A. aegypti and AeHKT inhibitors from in vitro and in silico studies. Here, we report the synthesis of new sodium 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] propanoates and the cognate HKT-inhibitory activity. These new derivatives act as competitive inhibitors with IC50 values in the range of 42 to 339

  控制埃及伊蚊种群最广泛使用的方法是化学控制方法。它代表了一种通过病媒控制来遏制多种疾病（例如登革热、寨卡、基孔肯雅热、黄热病）的省时且经济有效的方法。因此，为了最大限度地减少杀虫剂抗药性的上升，必须发现与现有化合物具有不同作用方式的新化合物。解毒酶是发现新杀虫剂的一个有吸引力的目标。犬尿氨酸途径是一条重要的代谢途径，它产生化学稳定的黄尿酸，由活性氧和氮物质的前体 3-羟基犬尿氨酸通过 3-羟基犬尿氨酸转氨酶 (HKT) 生物合成。此前，我们通过体外和计算机研究报道了 1,2,4-恶二唑衍生物作为埃及伊蚊和 AeHKT 抑制剂的杀幼剂的有效性。在这里，我们报道了新型 4-[3-(芳基)-1,2,4-恶二唑-5-基]丙酸钠的合成及其同源 HKT 抑制活性。这些新衍生物可作为竞争性抑制剂，IC 50值在 42 至 339 μM 范围内。我们进一步对我们小组先前报道的先前合成的4-[3-(芳基)-1
• Development of fluorinated CB2 receptor agonists for PET studies
  作者：Corinna Lueg、Dirk Schepmann、Robert Günther、Peter Brust、Bernhard Wünsch

  DOI：10.1016/j.bmc.2013.09.040

  日期：2013.12

  A convergent strategy was followed to modify systematically carbazole based CB2 receptor ligands. The length of the N-(fluoroalkyl) group (n in 7), the length of the alkanamide (m in 7) and the substitution pattern of the phenyl moiety (X and Y in 7) were varied systematically. The highest CB2 affinity was found for the 2-fluoroethyl substituted carbazole derivative 20a (K-i = 5.8 nM) containing the propionamide and the 2-bromo-4-fluorophenyl moiety. According to docking studies 20a fits nicely into the binding pocket of the CB2 receptor, but elongation of the fluoroethyl side chain leads to a different binding mode of the ligands. The high CB2 affinity together with the high selectivity over the CB2 subtype qualifies the fluoroethyl derivative 20a to be developed as a PET tracer. (C) 2013 Elsevier Ltd. All rights reserved.