4-fluoro-N-[(E)-3-(5-fluoro-1-imidazo[1,2-a]pyridin-2-ylmethyl-3-methyl-1H-indol-7-yl)acryloyl]benzenesulfonamide | 882998-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-fluoro-N-[(E)-3-(5-fluoro-1-imidazo[1,2-a]pyridin-2-ylmethyl-3-methyl-1H-indol-7-yl)acryloyl]benzenesulfonamide
• 英文别名: (E)-3-[5-fluoro-1-(imidazo[1,2-a]pyridin-2-ylmethyl)-3-methylindol-7-yl]-N-(4-fluorophenyl)sulfonylprop-2-enamide
• CAS: 882998-96-1
• 化学式: C₂₆H₂₀F₂N₄O₃S
• 分子量: 506.533
• InChiKey: SWFZBPQGMPYNOC-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-fluoro-N-[(E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)acryloyl]benzenesulfonamide 、 2-氯甲基咪唑并[1,2-a]吡啶盐酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以67%的产率得到4-fluoro-N-[(E)-3-(5-fluoro-1-imidazo[1,2-a]pyridin-2-ylmethyl-3-methyl-1H-indol-7-yl)acryloyl]benzenesulfonamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies Leading to the Identification of (2E)-3-[l-[(2,4-Dichlorophenyl)methyl]-5-fluoro-3-methyl-lH-indol-7-yl]-N-[(4,5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a Potent and Selective Prostanoid EP3 Receptor Antagonist, as a Novel Antiplatelet Agent That Does Not Prolong Bleeding

  摘要：

  The EP(3) receptor on the platelet mediates prostaglandin E(2) potentiation of thrombogenic coagonists including collagen and adenosine diphosphate (ADP). A pharmacophore driven approach led to the identification of diverse peri-substituted heterocycles as potent and selective EP(3) receptor antagonists. A simultaneous chemical optimization and druglike assessment of prioritized molecules converged oil a lead compound 50 (DG-041) that displayed favorable in vitro and functional activities as an inhibitor of human platelet aggregation. This agent is currently in human clinical trials for the treatment of atherothrombosis.

  DOI：

  10.1021/jm9005912