2'-(4-Iodobenzoyloxy)-5'-methylacetophenone | 1350428-72-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2'-(4-Iodobenzoyloxy)-5'-methylacetophenone
• 英文别名: (2-Acetyl-4-methylphenyl) 4-iodobenzoate
• CAS: 1350428-72-6
• 化学式: C₁₆H₁₃IO₃
• 分子量: 380.182
• InChiKey: JUKYBYGVAGGVMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-(4-Iodobenzoyloxy)-5'-methylacetophenone 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 hydrazine hydrate 、 potassium tert-butylate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 31.5h， 生成 5-dimethylamino-N-(3-(4-(3-(2-hydroxy-5-methylphenyl)-1H-pyrazol-5-yl)phenyl)-2-propynyl)-1-naphthalenesulfonamide
  参考文献：
  名称：

  Synthesis and Properties of Molecular Probes for the Rescue Site on Mutant Cystic Fibrosis Transmembrane Conductance Regulator

  摘要：

  Cystic fibrosis is a genetic disease caused by mutations in the gene for the cystic fibrosis transmembrane conductance regulator (CFTR) protein. In vitro experiments have demonstrated that 4-methyl-2-(5-phenyl-1H-pyrazol-3-yl)phenol (VRT-532, 1) is able to partially restore the function of mutant CFTR proteins. To help elucidate the nature of the interactions between 1 and mutant CFTR, molecular probes based on the structure of 1 have been prepared. These include a photoreactive aryl azide derivative 11 and a fluorescent dansyl sulfonamide 15. Additionally, a method for hydrogen isotope exchange on 1 has been developed, which could be used for the incorporation of radioactive tritium. Using iodide efflux assays, the probe molecules have been demonstrated to modulate the activity of mutant CFTR in the same manner as 1. These probe molecules enable a number of biochemical experiments aimed at understanding how 1 rescues the function of mutant CFTR. This understanding can in turn aid in the design and development of more efficacious compounds which may serve as therapeutic agents in the treatment of cystic fibrosis.

  DOI：

  10.1021/jm201335c
• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 、 4-碘苯甲酰氯 在 吡啶 作用下， 反应 1.0h， 以86%的产率得到2'-(4-Iodobenzoyloxy)-5'-methylacetophenone
  参考文献：
  名称：

  Synthesis and Properties of Molecular Probes for the Rescue Site on Mutant Cystic Fibrosis Transmembrane Conductance Regulator

  摘要：

  Cystic fibrosis is a genetic disease caused by mutations in the gene for the cystic fibrosis transmembrane conductance regulator (CFTR) protein. In vitro experiments have demonstrated that 4-methyl-2-(5-phenyl-1H-pyrazol-3-yl)phenol (VRT-532, 1) is able to partially restore the function of mutant CFTR proteins. To help elucidate the nature of the interactions between 1 and mutant CFTR, molecular probes based on the structure of 1 have been prepared. These include a photoreactive aryl azide derivative 11 and a fluorescent dansyl sulfonamide 15. Additionally, a method for hydrogen isotope exchange on 1 has been developed, which could be used for the incorporation of radioactive tritium. Using iodide efflux assays, the probe molecules have been demonstrated to modulate the activity of mutant CFTR in the same manner as 1. These probe molecules enable a number of biochemical experiments aimed at understanding how 1 rescues the function of mutant CFTR. This understanding can in turn aid in the design and development of more efficacious compounds which may serve as therapeutic agents in the treatment of cystic fibrosis.

  DOI：

  10.1021/jm201335c