4-aminophenyl-5-phenyl-1,2,4-oxadiazole | 54494-08-5

• 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-aminophenyl-5-phenyl-1,2,4-oxadiazole
• 英文别名: 4-(5-phenyl-1,2,4-oxadiazol-3-yl)aniline；3-(p-Aminophenyl)-5-phenyl-1,2,4-osadiazol；5-Phenyl-3-p-aminophenyl-1,2,4-oxadiazol；3-p-Aminophenyl-5-phenyl-1,2,4-oxadiazol；5-phenyl-3-(4-aminophenyl)-1,2,4-oxadiazole
• CAS: 54494-08-5
• 化学式: C₁₄H₁₁N₃O
• mdl: MFCD12529976
• 分子量: 237.261
• InChiKey: XPTIIOBBBMJBKM-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±47.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-aminophenyl-5-phenyl-1,2,4-oxadiazole 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 3-(4-azidophenyl)-5-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of Some Unusual (1,2,4-Oxadiazole)-Linked Hexenopyranosides and Mannopyranosides

  摘要：

  A copper-catalyzed reaction of propargyl 4,6-di-O-acetyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside with 3-(4-azidophenyl)-1,2,4-oxadiazoles gave the corresponding hexenopyranosides bearing an 1,2,4-oxadiazole subunit in the aglyconic part of the molecule. The same reaction between ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside and acetylenic 1,2,4-oxadiazoles afforded the corresponding hexenopyranosides carrying a triazole and a 1,2,4-oxadiazole ring at C-4 of the carbohydrate. Combination of the two sequences gave hexenopyranosides displaying two 1,2,4-oxadiazole subunits, each one being embedded in the C-1 and C-4 frameworks, of the carbohydrate moiety. A simple dihydroxylation reaction of these unsaturated carbohydrates yielded a series of mannopyranosides bearing one or two 1,2,4-oxadiazole subunits at C-1 or C-4. These new compounds were evaluated for their cytotoxic activities against two cell strains: NCI-H-292 (lung carcinoma) and Hep-2 (larynx carcinoma), some of them presenting impressive cell growth inhibitions.

  DOI：

  10.1080/07328300802120901
• 作为产物：
  描述：

  对氨基苯腈 在 盐酸羟胺 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 4-aminophenyl-5-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Discovery and synthesis of 1,2,4-oxadiazole derivatives as novel inhibitors of Zika, dengue, Japanese encephalitis, and classical swine fever virus infections

  摘要：

  寨卡病毒（ZIKV）是黄病毒科的一种虫媒病毒，由于与先天性畸形和严重的神经系统后遗症有关，已成为一个重大的公共卫生问题。因此，迫切需要开发有效的治疗方法来有效治疗 ZIKV 感染。本研究利用表型筛选鉴定了一系列具有抗 ZIKV 感染病毒活性的 1,2,4-恶二唑衍生物。随后，为此目的设计、合成和评估了28种新的衍生物。在这些化合物中，4-(5-苯基-1,2,4-恶二唑-3-基)-N-(吡啶-3-基甲基)苯胺(5d)对寨卡病毒感染具有有效的抗病毒活性。此外，结构-活性关系分析表明，该化合物苯胺氮上的苄基取代提高了效力，同时增强了其药物样特性。此外，5d 对对全球公共卫生具有重要意义的黄病毒科多种病毒（例如登革热、日本脑炎和猪瘟病毒）表现出抗病毒活性，表明其作为先导化合物用于生成具有广泛作用的 1,2,4-恶二唑衍生物的潜力。 -广谱抗黄病毒特性。

  DOI：

  10.1007/s12272-022-01380-8

文献信息

• [(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04003909A1

  公开（公告）日：1977-01-18

  Compounds of the formula ##STR1## and their acid-addition salts wherein X is O or S; R is hydrogen, lower alkyl, phenyl, chloro, bromo, trifluoromethyl, lower alkoxy, phenoxy, or di(lower alkyl)amino; R.sup.1 is hydrogen, lower alkyl, phenyl, substituted-phenyl, cycloalkyl, or heterocyclic; and R.sup.3 is lower alkyl, substituted-lower alkyl, cycloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl; are disclosed. These compounds exhibit anthelmintic and antibacterial and antifungal activity.

  该公式化合物及其酸盐，其中 X 为 O 或 S；R 为氢、较低烷基、苯基、氯、溴、三氟甲基、较低烷氧基、苯氧基或二(较低烷基)氨基；R.sup.1 为氢、较低烷基、苯基、取代苯基、环烷基或杂环基；R.sup.3 为较低烷基、取代较低烷基、环烷基、较低烯基、较低炔基、苯基或取代苯基。这些化合物具有驱虫、抗菌和抗真菌活性。
• 1,2,4-옥사디아졸 유도체 화합물 및 이를 유효성분으로 함유하는 항바이러스제
  申请人：Korea Disease Control and Prevention Agency 대한민국(질병관리청장)(219999015870)

  公开号：KR20210101636A

  公开（公告）日：2021-08-19

  본 발명은 1,2,4-옥사디아졸 유도체 화합물 및 이를 유효성분으로 함유하는 항바이러스제에 관한 것으로, 상기 화합물은 세포 독성이 없으면서도 항바이러스 활성을, 특히 항지카바이러스 활성을 가지고 있으므로, 항바이러스제로 유용하게 사용할 수 있다.

  本发明涉及1,2,4-噁二唑衍生物化合物及其作为有效成分含有抗病毒药物，所述化合物既具有无细胞毒性又具有抗病毒活性，特别是抗乙肝病毒活性，因此可用作抗病毒药物。
• Synthesis of glycosyl-triazole linked 1,2,4-oxadiazoles
  作者：Janaína V. dos Anjos、Denis Sinou、Sebastiao J. de Melo、Rajendra M. Srivastava

  DOI：10.1016/j.carres.2007.07.011

  日期：2007.11

  The synthesis of four different types of oxadiazoles containing a terminal acetylenic group is described. Reaction of these oxadiazoles with various azidoglycosides via a copper-catalyzed [3+2] cycloaddition ('click chemistry') afforded the corresponding glycosyl-triazole linked 1,2,4-oxadiazoles in good yields. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.
• US4003909A
  申请人：——

  公开号：US4003909A

  公开（公告）日：1977-01-18