4-[3-(5-Amino-1,3,4-oxadiazol-2-yl)-1,2-oxazol-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-(5-Amino-1,3,4-oxadiazol-2-yl)-1,2-oxazol-5-yl]phenol
• 化学式: C₁₁H₈N₄O₃
• 分子量: 244.21
• InChiKey: LEUWZZOBPSLMKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

文献信息

• SMALL MOLECULE-INHIBITORS OF 6-PHOSPHOFRUCTO-1-KINASE FOR REDUCING LACTATE GENERATION BY CANCER CELLS
  申请人：Kemijski Institut

  公开号：EP3833345A1

  公开（公告）日：2021-06-16
• [EN] SMALL MOLECULE-INHIBITORS OF 6-PHOSPHOFRUCTO-1-KINASE FOR REDUCING LACTATE GENERATION BY CANCER CELLS<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE 6-PHOSPHOFRUCTO-1-KINASE POUR RÉDUIRE LA GÉNÉRATION DE LACTATE PAR DES CELLULES CANCÉREUSES
  申请人：KEMIJSKI INST

  公开号：WO2020030613A1

  公开（公告）日：2020-02-13

  The present invention belongs to the field of compounds having therapeutic activity, more precisely to the field of compounds targeting the glycolytic pathway. The invention relates to seven compounds that dock to the ATP binding site of the cancer specific 6-phosphofructo-1-kinase (PFK1), inhibit its activity and significantly decrease redundant NADH formation and concomitantly lactate generation by the cancer cells. The targeted enzyme is believed to be the pivotal factor of deregulated glycolytic flux in cancer cells (Warburg effect) characterized by abundant lactate production that enables immune escape by cancer cells and triggers angiogenesis and metastases. The compounds are: - (2-[(5-benzo[1,3]dioxol-5-yl-1,3,4-oxadiazol-2-yl)sulfanyl]-N-isoxazol-3-yl-acetamide), - (3-methoxy-6-(3-1-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1H-pyrazol-3-yl}phenyl) pyridazine), - N-[5-(methanesulfonamido)-1,3,4-thiadiazol-2-yl]-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide), - (3-(4-chlorophenyl)sulfonyl-N-(5-isoxazol-5-yl-1,3,4-oxadiazol-2-yl)propanamide, - (4-[3-(5-amino-1,3,4-oxadiazol-2-yl)isoxazol-5-yl]phenol), - ((2R)-N-(5-isoxazol-5-yl-1,3,4-oxadiazol-2-yl)-2,3-dihydro-1,4-benzodioxine-2-carboxamide) and - (3-(benzenesulfonyl)-N-(5-isoxazol-5-yl-1,3,4-oxadiazol-2-yl)propanamide). These compounds inhibit the cancer-specific PFK enzyme and markedly reduce lactate production through reduced NADH generation, which decreases the necessity of NADH re-oxidation by forming lactate.