methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-2,5-dimethyl-3-thienyl]carbonyl}amino)ethyl]benzoate | 1207860-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-2,5-dimethyl-3-thienyl]carbonyl}amino)ethyl]benzoate
• 英文别名: methyl 4-[(1S)-1-[[4-[(3-chlorophenyl)methyl]-2,5-dimethylthiophene-3-carbonyl]amino]ethyl]benzoate
• CAS: 1207860-99-8
• 化学式: C₂₄H₂₄ClNO₃S
• 分子量: 441.978
• InChiKey: DUQNMUNTACNASX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-2,5-dimethyl-3-thienyl]carbonyl}amino)ethyl]benzoate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 17.0h， 以91%的产率得到4-[(1S)-1-[[[4-[(3-chlorophenyl)methyl]-2,5-dimethyl-3-thienyl]carbonyl]amino]ethyl]benzoic acid
  参考文献：
  名称：

  The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist

  摘要：

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.

  DOI：

  10.1021/jm901771h
• 作为产物：
  描述：

  4-(3-chlorobenzyl)-2,5-dimethylthiophene-3-carboxylic acid 、 (S)-4-(1-氨基乙基)-苯甲酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-2,5-dimethyl-3-thienyl]carbonyl}amino)ethyl]benzoate
  参考文献：
  名称：

  The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist

  摘要：

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.

  DOI：

  10.1021/jm901771h

文献信息

• THIOPHENECARBOXAMIDE DERIVATIVES AS EP4 RECEPTOR LIGANDS
  申请人：Blouin Marc

  公开号：US20090247596A1

  公开（公告）日：2009-10-01

  The invention is directed to thiophenecarboxamide derivatives of formulae I and II as EP4 receptor ligands, antagonists or agonists, useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis, cancer and glaucoma. Pharmaceutical compositions and methods of use are also included. (Formulas I and II).

  本发明涉及公式I和II的噻吩羧酰胺衍生物，作为EP4受体配体、拮抗剂或激动剂，用于治疗EP4介导的疾病或症状，如急性和慢性疼痛、骨关节炎、类风湿性关节炎、癌症和青光眼。还包括药物组合物和使用方法。(公式I和II)
• The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist
  作者：Marc Blouin、Yongxin Han、Jason Burch、Julie Farand、Christophe Mellon、Mireille Gaudreault、Mark Wrona、Jean-François Lévesque、Danielle Denis、Marie-Claude Mathieu、Rino Stocco、Erika Vigneault、Alex Therien、Patsy Clark、Steve Rowland、Daigen Xu、Gary O’Neill、Yves Ducharme、Rick Friesen

  DOI：10.1021/jm901771h

  日期：2010.3.11

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.