3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenol | 171368-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenol
• 英文别名: 3,4'-(1,3,4-oxadiazole-2,5-diyl)diphenol；3-[5-(4-Hydroxyphenyl)-1,3,4-oxadiazol-2-yl]phenol；3-[5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]phenol
• CAS: 171368-15-3
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: NOXMLKDKEYSUKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  79.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-hydroxybenzoic acid N'-(3-hydroxybenzoyl)-hydrazide 在 吡啶 、 氯化亚砜 作用下， 反应 5.0h， 以550 mg的产率得到3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Stilbene analogs as inducers of apolipoprotein-I transcription

  摘要：

  Based on the naturally occurring stilbene, Resveratrol, a series of novel stilbene derivatives were synthesized, which have the ability to induce the expression of the ApoA-I gene. Several compounds equally or more potent than Resveratrol were identified. trans-4,4'-Dihydroxy-2-methoxystilbene was the most potent (4.6x more potent than Resveratrol). These compounds provide an early lead into new drugs to treat atherosclerosis. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.076

文献信息

• Synthesis, in silico analysis and antidepressant activity of 1,3,4-oxadiazole derivatives
  作者：Banylla Felicity Dkhar Gatphoh、Natasha Naval Aggarwal、S. Madan Kumar、M. Vijay Kumar、B. C. Revanasiddappa

  DOI：10.3329/bjp.v17i1.58728

  日期：——

  The compounds 1,3,4-oxadiazole derivatives (1-8) were synthesized by the cyclization of 4-hydroxy benzhydrazide (1) with various substituted aroma-tic aldehydes (2) using FeCl3 as catalyst and methanol as a solvent medium. The structures of the newly synthesized compounds were assigned based on FT-IR, 1H-NMR, and mass spectral data. In vivo antidepressant activity was performed by tail suspension test and forced swimming test models. Using the Schrodinger Maestro, the in silico analysis was performed and docked to the glycogen synthase kinase 3β binding site (PDB: 3GB2). Compounds 8 [4,4'-(1,3,4-oxadiazole-2,5-diyl)diphenol] and 3 [3-(5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl) phenol] showed both potent inhibitory activity against GSK-3β with a docking score of -7.800 kcal/mol as well as good antidepressant activity in both tail suspension and forced swimming tests models. The synthesized derivatives showed good antidepressive potential.

  化合物1,3,4-噁二唑衍生物（1-8）通过4-羟基苯基肼（1）与不同取代芳香醛（2）在FeCl3催化和甲醇溶剂介质下环化合成。新合成化合物的结构基于FT-IR，1H-NMR和质谱数据进行了确定。采用Schrodinger Maestro进行了体外抗抑郁活性评估，包括尾悬试验和强制游泳试验模型。通过对糖原合成酶激酶3β结合位点（PDB：3GB2）进行分子对接，进行了体外分析。化合物8 [4,4'-(1,3,4-噁二唑-2,5-二基)二苯酚]和3 [3-(5-(4-羟基苯基)-1,3,4-噁二唑-2-基)苯酚] 表现出对GSK-3β的强抑制活性，对接分数为-7.800 kcal/mol，并且在尾悬试验和强制游泳试验模型中表现出良好的抗抑郁活性。合成的衍生物显示出良好的抗抑郁潜力。
• Stilbene analogs as inducers of apolipoprotein-I transcription
  作者：Henrik C. Hansen、Fabrizio S. Chiacchia、Reena Patel、Norman C.W. Wong、Vladimir Khlebnikov、Renata Jankowska、Kalpesh Patel、M. Madhava Reddy

  DOI：10.1016/j.ejmech.2009.12.076

  日期：2010.5

  Based on the naturally occurring stilbene, Resveratrol, a series of novel stilbene derivatives were synthesized, which have the ability to induce the expression of the ApoA-I gene. Several compounds equally or more potent than Resveratrol were identified. trans-4,4'-Dihydroxy-2-methoxystilbene was the most potent (4.6x more potent than Resveratrol). These compounds provide an early lead into new drugs to treat atherosclerosis. (C) 2010 Elsevier Masson SAS. All rights reserved.