5-azido-2-hydroxyacetophenone | 1332713-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-2-hydroxyacetophenone
• 英文别名: 1-(5-Azido-2-hydroxyphenyl)ethanone；1-(5-azido-2-hydroxyphenyl)ethanone
• CAS: 1332713-50-4
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: KAGPMGRBQNDVOO-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azido-2-hydroxyacetophenone 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 6-azidoflavonol
  参考文献：
  名称：

  Synthesis of a hypoxia-targeted conjugate of the cardioprotective agent 3′,4′-dihydroxyflavonol and evaluation of its ability to reduce ischaemia/reperfusion injury

  摘要：

  3',4'-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that reduces injury associated with myocardial ischaemia and reperfusion. We hypothesized that the efficacy of DiOHF could be enhanced through its targeting to hypoxic regions of partial reperfusion. Copper(I)-catalyzed ligation of an azide-modified DiOHF analogue to 2-propargyl-nitroimidazole afforded a DiOHF-nitroimidazole conjugate (DiOHF-NIm). When incubated with Con8 cells under normoxic conditions DiOHF-NIm could be detected in both the culture supernatant and cell lysate, whereas under hypoxic conditions it was present in substantially reduced amounts consistent with its selective metabolism under hypoxia. DiOHF-NIm possessed antioxidant activity comparable to DiOHF through scavenging of superoxide produced by NADPH/NADPH oxidase, but had significantly attenuated vasorelaxant activity. DiOHF-NIm treatment significantly reduced lactate dehydrogenase release following ischaemia/reperfusion in hindlimbs of anaesthetized rats (p < 0.05), to a level similar to DiOHF treatment but also at earlier time points. DiOHF-NIm significantly reduced levels of myeloperoxidase (p < 0.05), a biomarker of neutrophil accumulation, whereas the reduction afforded by DiOHF was not significant. DiOHF-NIm therefore represents a promising potential therapeutic for ischaemia/reperfusion injury. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.040
• 作为产物：
  描述：

  5-氨基-2-羟基苯乙酮 在 硫酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 1.5h， 以91%的产率得到5-azido-2-hydroxyacetophenone
  参考文献：
  名称：

  单击化学合成，生物学评估以及对一些新型2'-羟基查尔酮-三唑杂化物作为有效的抗炎剂的对接研究。

  摘要：

  杂交药效团方法用于设计和合成两个新颖的2'-羟基查耳酮-三唑杂化分子系列6a-j和8a-j。这些化合物已通过光谱和元素分析充分表征。在体外和体内对它们的抗炎活性进行了评估。大多数化合物是COX-2的选择性抑制剂。其中，化合物6d，6f，6i，8c，8e和8h表现出对COX-2（IC50 = 0.037-0.041 µM）和15-LOX（IC50 = 1.41-1.80 µM）的双重有效抑制。化合物6i，8c和8h显示塞来昔布的体内抗炎活性为116％，113％和109％。因此，化合物6d，6f，6i，8c，8e和8h-j是COX-2和15-LOX的有效双重抑制剂。对COX-2和15-LOX活性位点的对接研究可确保结合亲和力和选择性。

  DOI：

  10.1016/j.bioorg.2019.103505

文献信息

• Synthesis of a hypoxia-targeted conjugate of the cardioprotective agent 3′,4′-dihydroxyflavonol and evaluation of its ability to reduce ischaemia/reperfusion injury
  作者：Suwan Yap、Owen L. Woodman、Peter J. Crack、Spencer J. Williams

  DOI：10.1016/j.bmcl.2011.03.040

  日期：2011.9

  3',4'-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that reduces injury associated with myocardial ischaemia and reperfusion. We hypothesized that the efficacy of DiOHF could be enhanced through its targeting to hypoxic regions of partial reperfusion. Copper(I)-catalyzed ligation of an azide-modified DiOHF analogue to 2-propargyl-nitroimidazole afforded a DiOHF-nitroimidazole conjugate (DiOHF-NIm). When incubated with Con8 cells under normoxic conditions DiOHF-NIm could be detected in both the culture supernatant and cell lysate, whereas under hypoxic conditions it was present in substantially reduced amounts consistent with its selective metabolism under hypoxia. DiOHF-NIm possessed antioxidant activity comparable to DiOHF through scavenging of superoxide produced by NADPH/NADPH oxidase, but had significantly attenuated vasorelaxant activity. DiOHF-NIm treatment significantly reduced lactate dehydrogenase release following ischaemia/reperfusion in hindlimbs of anaesthetized rats (p < 0.05), to a level similar to DiOHF treatment but also at earlier time points. DiOHF-NIm significantly reduced levels of myeloperoxidase (p < 0.05), a biomarker of neutrophil accumulation, whereas the reduction afforded by DiOHF was not significant. DiOHF-NIm therefore represents a promising potential therapeutic for ischaemia/reperfusion injury. (c) 2011 Elsevier Ltd. All rights reserved.
• Click chemistry synthesis, biological evaluation and docking study of some novel 2′-hydroxychalcone-triazole hybrids as potent anti-inflammatory agents
  作者：Andrew N. Boshra、Hajjaj H.M. Abdu-Allah、Anber F. Mohammed、Alaa M. Hayallah

  DOI：10.1016/j.bioorg.2019.103505

  日期：2020.1

  A hybrid pharmacophore approach is used to design and synthesize two novel series of 2'-hydroxychalcone-triazole hybrid molecules 6a-j and 8a-j. These compounds were fully characterized by spectral and elemental analyses. They were evaluated in vitro and in vivo for anti-inflammatory activity. Most of compounds were selective inhibitors for COX-2. Among them, compounds 6d, 6f, 6i, 8c, 8e and 8h demonstrated

  杂交药效团方法用于设计和合成两个新颖的2'-羟基查耳酮-三唑杂化分子系列6a-j和8a-j。这些化合物已通过光谱和元素分析充分表征。在体外和体内对它们的抗炎活性进行了评估。大多数化合物是COX-2的选择性抑制剂。其中，化合物6d，6f，6i，8c，8e和8h表现出对COX-2（IC50 = 0.037-0.041 µM）和15-LOX（IC50 = 1.41-1.80 µM）的双重有效抑制。化合物6i，8c和8h显示塞来昔布的体内抗炎活性为116％，113％和109％。因此，化合物6d，6f，6i，8c，8e和8h-j是COX-2和15-LOX的有效双重抑制剂。对COX-2和15-LOX活性位点的对接研究可确保结合亲和力和选择性。