thiophene-2-sulfonic acid [(E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)acryloyl]amide | 882999-51-1

• 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: thiophene-2-sulfonic acid [(E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)acryloyl]amide
• 英文别名: (E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)-N-thiophen-2-ylsulfonylprop-2-enamide
• CAS: 882999-51-1
• 化学式: C₁₆H₁₃FN₂O₃S₂
• 分子量: 364.421
• InChiKey: XKAIDNZXUJOAST-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  thiophene-2-sulfonic acid [(E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)acryloyl]amide 、 2-溴甲基萘 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以90%的产率得到thiophene-2-sulfonic acid [(E)-3-(5-fluoro-3-methyl-1-naphthalen-2-ylmethyl-1H-indol-7-yl)acryloyl]amide
  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：

  2-噻吩磺酰胺 、 (2E)-3-(5-氟-3-甲基-1H-吲哚-7-基)-2-丙烯酸 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60%的产率得到thiophene-2-sulfonic acid [(E)-3-(5-fluoro-3-methyl-1H-indol-7-yl)acryloyl]amide
  参考文献：
  名称：

  Sulfonamide peri-substituted bicyclics for occlusive artery disease

  摘要：

  酰基磺酰胺，带有周取代的融合双环环化合物，用于治疗或预防前列腺素介导的疾病或症状。这些化合物的一般公式为 代表性示例是：

  公开号：

  US20060079520A1

文献信息

• Sulfonamide peri-substituted bicyclics for occlusive artery disease
  申请人：Singh Jasbir

  公开号：US20060079520A1

  公开（公告）日：2006-04-13

  Acyl sulfonamide, peri-substituted, fused bicyclic ring compounds useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed. The compounds are of the general formula A representative example is:

  酰基磺酰胺，带有周取代的融合双环环化合物，用于治疗或预防前列腺素介导的疾病或症状。这些化合物的一般公式为 代表性示例是：
• SULFONAMIDE PERI-SUBSTITUTED BICYCLICS FOR OCCLUSIVE ARTERY DISEASE
  申请人：DECODE GENETICS, EHF

  公开号：EP1812388B1

  公开（公告）日：2011-02-23
• Structure−Activity Relationship Studies Leading to the Identification of (2<i>E</i>)-3-[l-[(2,4-Dichlorophenyl)methyl]-5-fluoro-3-methyl-l<i>H</i>-indol-7-yl]-<i>N</i>-[(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
  作者：Jasbir Singh、Wayne Zeller、Nian Zhou、Georgeta Hategan、Rama K. Mishra、Alex Polozov、Peng Yu、Emmanuel Onua、Jun Zhang、José L. Ramírez、Gudmundur Sigthorsson、Margret Thorsteinnsdottir、Alex. S. Kiselyov、David E. Zembower、Thorkell Andrésson、Mark E. Gurney

  DOI：10.1021/jm9005912

  日期：2010.1.14

  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.