methyl (2E)-3-(1'-methyl-2'-oxo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indol]-4'-yl)prop-2-enoate | 883000-68-8

• 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: methyl (2E)-3-(1'-methyl-2'-oxo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indol]-4'-yl)prop-2-enoate
• CAS: 883000-68-8
• 化学式: C₁₅H₁₅NO₅
• 分子量: 289.288
• InChiKey: OSZHMWJZBWKPDL-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-(1'-methyl-2'-oxo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indol]-4'-yl)prop-2-enoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到(2E)-3-(1'-methyl-2'-oxo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indol]-4'-yl)prop-2-enoic 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
• 作为产物：
  描述：

  methyl (2E)-3-(2'-oxo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indol]-4'-yl)prop-2-enoate 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以80%的产率得到methyl (2E)-3-(1'-methyl-2'-oxo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indol]-4'-yl)prop-2-enoate
  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