4,5-dibromo-2-(4-(trifluoromethoxy)phenyl)pyridazin-3(2H)-one | 1549708-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-dibromo-2-(4-(trifluoromethoxy)phenyl)pyridazin-3(2H)-one
• 英文别名: 4,5-Dibromo-2-[4-(trifluoromethoxy)phenyl]pyridazin-3-one
• CAS: 1549708-76-0
• 化学式: C₁₁H₅Br₂F₃N₂O₂
• 分子量: 413.976
• InChiKey: HEXBHKDEEFLBPJ-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-2-(4-(trifluoromethoxy)phenyl)pyridazin-3(2H)-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到5-azido-4-bromo-2-(4-(trifluoromethoxy)phenyl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3)

  摘要：

  High-throughput screening of a small-molecule library identified a 5-triazolo-2-arylpyridazinone as a novel inhibitor of the important glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3). Such inhibitors are of interest due to PFKFB3's control of the important glycolytic pathway used by cancer cells to generate ATP. A series of analogues was synthesized to study structure-activity relationships key to enzyme inhibition. Changes to the triazolo or pyridazinone rings were not favoured, but limited-size substitutions on the aryl ring provided modest increases in potency against the enzyme. Selected analogues and literature-described inhibitors were evaluated for their ability to suppress the glycolytic pathway, as detected by a decrease in lactate production, but none of these compounds demonstrated such suppression at non-cytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.041
• 作为产物：
  描述：

  (2E)-2,3-dibromo-4-oxobut-2-enoic acid 、 4-三氟甲氧基苯肼盐酸盐 在 盐酸 作用下， 以 水 为溶剂， 反应 16.5h， 以4.327 g的产率得到4,5-dibromo-2-(4-(trifluoromethoxy)phenyl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3)

  摘要：

  High-throughput screening of a small-molecule library identified a 5-triazolo-2-arylpyridazinone as a novel inhibitor of the important glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3). Such inhibitors are of interest due to PFKFB3's control of the important glycolytic pathway used by cancer cells to generate ATP. A series of analogues was synthesized to study structure-activity relationships key to enzyme inhibition. Changes to the triazolo or pyridazinone rings were not favoured, but limited-size substitutions on the aryl ring provided modest increases in potency against the enzyme. Selected analogues and literature-described inhibitors were evaluated for their ability to suppress the glycolytic pathway, as detected by a decrease in lactate production, but none of these compounds demonstrated such suppression at non-cytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.041