2-叠氮基-1-(2,4-二氟苯基)乙酮 | 1041193-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-叠氮基-1-(2,4-二氟苯基)乙酮
• 英文名称: 2-azido-1-(2,4-difluorophenyl)ethanone
• 英文别名: 1-(2,4-Difluorophenyl)-2-azidoethanone
• CAS: 1041193-41-2
• 化学式: C₈H₅F₂N₃O
• 分子量: 197.144
• InChiKey: FEZAYPDYYMXHIE-UHFFFAOYSA-N

物化性质

• 熔点：
  34-35 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-叠氮基-1-(2,4-二氟苯基)乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-azido-1-(2,4-difluorophenyl)ethan-1-ol
  参考文献：
  名称：

  Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities

  摘要：

  A series of novel piperazine-1,2,3-triazole derivatives, which entailed the bioisosteric replacement of the imidazole moiety and hybridization of two drug scaffolds was prepared by employing the regioselective copper (I)-catalysed azide-alkyne 1,3-dipolar cycloaddition reaction. The synthesized compounds were evaluated for antibacterial activities against Gram-negative (E. Coli and P. Putida), Gram-positive S. Aureus bacteria and fungicidal activities against F. oxysporum, F. gramillarium and F. monalliforme fungi. Compound 7ac' exhibited moderate but promising antibacterial activity against Gram-negative bacteria and fungicidal activity against F. oxysporum and F. gramillarium.

  DOI：

  10.1007/s00044-015-1361-5
• 作为产物：
  描述：

  2',4'-二氟苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-叠氮基-1-(2,4-二氟苯基)乙酮
  参考文献：
  名称：

  Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities

  摘要：

  A series of novel piperazine-1,2,3-triazole derivatives, which entailed the bioisosteric replacement of the imidazole moiety and hybridization of two drug scaffolds was prepared by employing the regioselective copper (I)-catalysed azide-alkyne 1,3-dipolar cycloaddition reaction. The synthesized compounds were evaluated for antibacterial activities against Gram-negative (E. Coli and P. Putida), Gram-positive S. Aureus bacteria and fungicidal activities against F. oxysporum, F. gramillarium and F. monalliforme fungi. Compound 7ac' exhibited moderate but promising antibacterial activity against Gram-negative bacteria and fungicidal activity against F. oxysporum and F. gramillarium.

  DOI：

  10.1007/s00044-015-1361-5

文献信息

• Synthesis of Optically Pure 2-Azido-1-arylethanols with Isolated Enzymes and Conversion to Triazole-Containing β-Blocker Analogues Employing Click Chemistry
  作者：Haribabu Ankati、Yan Yang、Dunming Zhu、Edward R. Biehl、Ling Hua

  DOI：10.1021/jo8009616

  日期：2008.8.1

  α-azidoacetophenone derivatives catalyzed by a recombinant carbonyl reductase from Candida magnoliae (CMCR) or an alcohol dehydrogenase from Saccharomyces cerevisiae (Ymr226c). This provides an effective route to this class of important compounds in optically pure form. (S)-2-Azido-1-(p-chlorophenyl)ethanols reacted with alkynes employing click chemistry to afford high yields of optically pure triazole-containing

  合成了2-叠氮基-1-芳基乙醇的两种对映体，均通过酶促还原木薯假丝酵母（CMCR）的重组羰基还原酶或酿酒酵母（Ymr226c）的醇脱氢酶催化的相应α-叠氮苯乙酮衍生物而获得了极佳的光学纯度。这为光学纯形式的这类重要化合物提供了有效的途径。（S）-2-叠氮基-1-（对氯苯基）乙醇与炔烃利用点击化学反应，得到高产率的具有潜在生物活性的光学纯的含三唑的β-肾上腺素能受体阻滞剂类似物。
• Synthesis and Biological Evaluation of <i>N</i>-Aryl-5-aryloxazol-2-amine Derivatives as 5-Lipoxygenase Inhibitors
  作者：Jee Hee Suh、Eul Kgun Yum、Young Sik Cho

  DOI：10.1248/cpb.c15-00033

  日期：——

  We describe the synthesis and biological evaluation of N-aryl-5-aryloxazol-2-amine derivatives that are able to inhibit 5-lipoxygenase (5-LOX), a key enzyme of leukotriene synthesis, for the treatment of inflammation-related diseases including asthma and rheumatoid arthritis. A novel structural moiety containing oxazole was initially identified from a chemical library using an in vitro enzymatic and cell-based assay, and its synthesized oxazole derivatives were further examined to develop a structure–activity relationship (SAR). SAR analysis demonstrated that a hydroxyl or amino group at the p-position on N-phenyl was essential for the 5-LOX-inhibitory activities of the derivatives, and that other halogen and methyl group-substituted derivatives affected the potency, positively or negatively. As a result, derivatives selected through first-round screening were further optimized using a cell-based assay and an in vivo assay to develop a potent, selective 5-LOX inhibitor. A final hit exhibited an improved efficacy in arachidonic acid-induced ear edema when applied topically but not orally. Moreover, it showed the additional advantage of sustainable antiinflammatory activity over a reference compound, zileuton. Taken together, chemical entities bearing an oxazole scaffold could be promising as therapeutic drugs for the treatment of chronic inflammatory skin disorders.

  我们描述了能够抑制白三烯合成关键酶 5-脂氧合酶（5-LOX）的 N-芳基-5-芳基恶唑-2-胺衍生物的合成和生物学评价，这些衍生物可用于治疗包括哮喘和类风湿性关节炎在内的炎症相关疾病。利用体外酶促和细胞检测法从化学库中初步鉴定出了一种含有噁唑的新型结构分子，并进一步研究了其合成的噁唑衍生物，以建立结构-活性关系（SAR）。SAR 分析表明，N-苯基 p 位上的羟基或氨基对衍生物的 5-LOX 抑制活性至关重要，而其他卤素和甲基取代的衍生物会对药效产生或正或负的影响。因此，通过第一轮筛选选出的衍生物利用细胞检测和体内检测进行了进一步优化，以开发出一种强效、选择性的 5-LOX 抑制剂。最终发现的一种衍生物在花生四烯酸诱发的耳部水肿方面具有更好的疗效。此外，与参考化合物齐鲁通（zileuton）相比，它还具有持续抗炎活性的额外优势。综上所述，含有噁唑支架的化学实体有望成为治疗慢性皮肤炎症的药物。