(RS)-4-(3-thienyl)phenyl-α-methyl acetic acid | 678173-92-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (RS)-4-(3-thienyl)phenyl-α-methyl acetic acid
• 英文别名: S-4-(3-thienyl)phenyl-α-methylacetic acid；Atliprofen, (S)-；(2S)-2-(4-thiophen-3-ylphenyl)propanoic acid
• CAS: 678173-92-7
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: PFLCZHOSQMPCMN-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(3-thienyl)-α-methylbenzylbromide 在 盐酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (RS)-4-(3-thienyl)phenyl-α-methyl acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of S -4-(3-thienyl)phenyl-α-methylacetic acid

  摘要：

  Herein we report an efficient procedure to synthesize S-4-(3-thienyl)phenyl-alpha-methylacetic acid, an enantiomerically pure intermediate of a recently approved nonsteroidal antiinflammatory cyclooxygenase inhibitor, atliprofen [methyl RS-4-(3-thienyl)phenyl-alpha-methylacetate]. The interactions of the active S-isomer of the acid were theoretically compared with those of S-ibuprofen through molecular docking studies using COX-1 and COX-2 protein structures. The results were corroborated by in vitro and in vivo studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.066

文献信息

• Synthesis and evaluation of S -4-(3-thienyl)phenyl-α-methylacetic acid
  作者：Shilpi Mittal、Alpeshkumar Malde、C. Selvam、K.H.S. Arun、P.S. Johar、Sanjay M. Jachak、P. Ramarao、P.V. Bharatam、H.P.S. Chawla

  DOI：10.1016/j.bmcl.2003.11.066

  日期：2004.2

  Herein we report an efficient procedure to synthesize S-4-(3-thienyl)phenyl-alpha-methylacetic acid, an enantiomerically pure intermediate of a recently approved nonsteroidal antiinflammatory cyclooxygenase inhibitor, atliprofen [methyl RS-4-(3-thienyl)phenyl-alpha-methylacetate]. The interactions of the active S-isomer of the acid were theoretically compared with those of S-ibuprofen through molecular docking studies using COX-1 and COX-2 protein structures. The results were corroborated by in vitro and in vivo studies. (C) 2003 Elsevier Ltd. All rights reserved.