(E)-3-[1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indol-7-yl]acrylic acid | 1202714-35-9

• 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: (E)-3-[1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indol-7-yl]acrylic acid
• 英文别名: (E)-3-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-5-fluoro-3-methylindol-7-yl]prop-2-enoic acid
• CAS: 1202714-35-9
• 化学式: C₂₁H₁₈FNO₄
• 分子量: 367.377
• InChiKey: USGBAMGXEQGEIO-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲磺酰胺 、 (E)-3-[1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indol-7-yl]acrylic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到N-{(E)-3-[1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indol-7-yl]acryloyl}-C,C,C-trifluoromethanesulfonamide
  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
• 作为产物：
  描述：

  (E)-3-[1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indol-7-yl]acrylic acid methyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以87%的产率得到(E)-3-[1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-5-fluoro-3-methyl-1H-indol-7-yl]acrylic acid
  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