4-(3-bromo-4,5-dihydroisoxazol-5-yl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(3-bromo-4,5-dihydroisoxazol-5-yl)phenol
• 英文别名: 4-(3-Bromo-4,5-dihydro-1,2-oxazol-5-yl)phenol；4-(3-bromo-4,5-dihydro-1,2-oxazol-5-yl)phenol
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: JBFXRILLHFSHIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 4-羟基苯乙烯 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以78%的产率得到4-(3-bromo-4,5-dihydroisoxazol-5-yl)phenol
  参考文献：
  名称：

  Discovery of Covalent Inhibitors of Glyceraldehyde-3-phosphate Dehydrogenase, A Target for the Treatment of Malaria

  摘要：

  We developed a new class of covalent inhibitors of Plasmodium falciparum glyceraldehyde-3-phosphate dehydrogenase, a validated target for the treatment of malaria, by screening a small library of 3-bromo-isoxazoline derivatives that inactivate the enzyme through a covalent, selective bond to the catalytic cysteine, as demonstrated by mass spectrometry. Substituents on the isoxazolinic ring modulated the potency up to 20-fold, predominantly due to an electrostatic effect, as assessed by computational analysis.

  DOI：

  10.1021/jm500747h

文献信息

• Discovery of Covalent Inhibitors of Glyceraldehyde-3-phosphate Dehydrogenase, A Target for the Treatment of Malaria
  作者：Stefano Bruno、Andrea Pinto、Gianluca Paredi、Lucia Tamborini、Carlo De Micheli、Valeria La Pietra、Luciana Marinelli、Ettore Novellino、Paola Conti、Andrea Mozzarelli

  DOI：10.1021/jm500747h

  日期：2014.9.11

  We developed a new class of covalent inhibitors of Plasmodium falciparum glyceraldehyde-3-phosphate dehydrogenase, a validated target for the treatment of malaria, by screening a small library of 3-bromo-isoxazoline derivatives that inactivate the enzyme through a covalent, selective bond to the catalytic cysteine, as demonstrated by mass spectrometry. Substituents on the isoxazolinic ring modulated the potency up to 20-fold, predominantly due to an electrostatic effect, as assessed by computational analysis.