2-(4-fluorophenyl)-2-(4-methylsulfonylbenzoyl)acetic acid ethyl ester | 329076-64-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-fluorophenyl)-2-(4-methylsulfonylbenzoyl)acetic acid ethyl ester
• 英文别名: Ethyl 2-(4-fluorophenyl)-3-(4-(methylsulphonyl)phenyl)-3-oxopropanoate；2-(4-fluorophenyl)-3-(4-methanesulfonylphenyl)-3-oxo-propionic acid ethyl ester；Ethyl 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-3-oxopropanoate
• CAS: 329076-64-4
• 化学式: C₁₈H₁₇FO₅S
• 分子量: 364.394
• InChiKey: DWZXDPPPNGLUDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-2-(4-methylsulfonylbenzoyl)acetic acid ethyl ester 在 potassium carbonate 、 对甲苯磺酸 、 一水合肼 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 3-Ethyl-7-(4-fluorophenyl)-6-(4-(methylsulphonyl)phenyl)pyrazolo[5,1-b][1,3]oxazole
  参考文献：
  名称：

  Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors

  摘要：

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

  DOI：

  10.1021/jo049264k
• 作为产物：
  描述：

  4-氟苯乙酸 在 硫酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 2-(4-fluorophenyl)-2-(4-methylsulfonylbenzoyl)acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol Derivatives as Potential COX-2 Inhibitors

  摘要：

  4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diaryl-pyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

  DOI：

  10.1021/jo049264k

文献信息

• [EN] THIONE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] DERIVES DE THIONE, LEURS PROCEDES DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：CJ CORP

  公开号：WO2005051941A1

  公开（公告）日：2005-06-09

  A 1,2,4-triazole derivative of formula (1) or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

  本发明提供了一种式(1)的1,2,4-三唑衍生物或其非毒性盐，其制备方法以及含有该衍生物或盐作为活性成分的药物组合物。
• Thione Derivative, Method For The Preparation Thereof, And Pharmaceutical Composition Containing The Same
  申请人：Cho Il Hwan

  公开号：US20080090875A1

  公开（公告）日：2008-04-17

  A 1,2,4-triazole derivative of formula 1 or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

  提供了公式1的1,2,4-三唑衍生物或其非毒性盐的制备方法，以及含有该衍生物或盐作为活性成分的药物组合物。
• SULFONYLPHENYLPYRAZOLE COMPOUNDS USEFUL AS COX-2 INHIBITORS
  申请人：ABBOTT LABORATORIES

  公开号：EP1206474B1

  公开（公告）日：2004-05-26
• US6472416B1
  申请人：——

  公开号：US6472416B1

  公开（公告）日：2002-10-29
• US7781592B2
  申请人：——

  公开号：US7781592B2

  公开（公告）日：2010-08-24