4-Methylsulfanyl-[1,1';2',1'']terphenyl | 178817-00-0

• 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: 4-Methylsulfanyl-[1,1';2',1'']terphenyl
• 英文别名: 1-Methylsulfanyl-4-(2-phenylphenyl)benzene
• CAS: 178817-00-0
• 化学式: C₁₉H₁₆S
• 分子量: 276.402
• InChiKey: GRXSCADREKLSOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-Methylsulfanyl-[1,1';2',1'']terphenyl 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到2-[4-(methylsulfonyl)phenyl]-1-phenylbenzene
  参考文献：
  名称：

  Terphenyl cyclooxygenase-2 (COX-2) inhibitors: Optimization of the central ring and o-biphenyl analogs

  摘要：

  The discovery of terphenyl derivatives as highly selective COX-2 inhibitors resulted from our efforts to overcome poor pharmacokinetics demonstrated by the COX-2 selective diarylthiophene DuP 697 [2-bromo-4-(4'-sulfonylmethyl)phenyl-5-(4'-fluoro)phenylthiophene]. Detailed SAR related to the ortho-biphenyls and variants of the central ring are described herein. (C) 1999 DuPont Pharmaceuticals. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00105-5
• 作为产物：
  描述：

  4-溴苯基三氟甲基磺酸酯 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 4-Methylsulfanyl-[1,1';2',1'']terphenyl
  参考文献：
  名称：

  Terphenyl cyclooxygenase-2 (COX-2) inhibitors: Optimization of the central ring and o-biphenyl analogs

  摘要：

  The discovery of terphenyl derivatives as highly selective COX-2 inhibitors resulted from our efforts to overcome poor pharmacokinetics demonstrated by the COX-2 selective diarylthiophene DuP 697 [2-bromo-4-(4'-sulfonylmethyl)phenyl-5-(4'-fluoro)phenylthiophene]. Detailed SAR related to the ortho-biphenyls and variants of the central ring are described herein. (C) 1999 DuPont Pharmaceuticals. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00105-5

文献信息

• Chemistry and pharmacokinetics of diarylthiophenes and terphenyls as selective COX-2 inhibitors
  作者：Donald J.P. Pinto、Robert A. Copeland、Maryanne B. Covington、William J. Pitts、Douglas G. Batt、Michael J. Orwat、Gilbert N. Lam、Amita Joshi、Yuk-Charn Chan、Shuaige Wang、James M. Trzaskos、Ronald L. Magolda、David M. Kornhauser

  DOI：10.1016/s0960-894x(96)00513-6

  日期：1996.12

  DuP697, 2-bromo-4-(4'-sulfonylmethyl)phenyl-5-(4'-fluoro)phenylthiophene, is a selective type 2 cyclooxygenase (COX-2) inhibitor. Its relatively weak COX-2 selectivity coupled with a poor human pharmacokinetic profile led us to seek improvements on the in vitro selectivity while at the same time, addressing some of its pharmacokinetic liabilities. In this paper we discuss some strategies at solving the PK issue within a class of COX-2 inhibitors. The result of these efforts led to the discovery of a new class of COX-2 inhibitors the terphenyls, which prove to be superior alternatives to the diarylthiophenes. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd
• NOVEL PROSTAGLANDIN SYNTHASE INHIBITORS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0783486A1

  公开（公告）日：1997-07-16
• US5593994A
  申请人：——

  公开号：US5593994A

  公开（公告）日：1997-01-14
• US5932586A
  申请人：——

  公开号：US5932586A

  公开（公告）日：1999-08-03
• [EN] NOVEL PROSTAGLANDIN SYNTHASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE LA PROSTAGLANDINE-SYNTHASE
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1996010012A1

  公开（公告）日：1996-04-04

  (EN) This invention relates to ortho substituted phenyl compounds as inhibitors of prostaglandin synthase, to pharmaceutical compositions comprising such compounds and to methods of using such compounds as antiinflammatory and antipyretic agents. The class of compounds useful in this method of treatment is represented by formula (I).(FR) L'invention porte sur des composés phényliques orthosubstitués inhibiteurs de la prostaglandine-synthase, sur des préparations pharmaceutiques contenant lesdits composés et sur leur mode d'utilisation comme agents anti-inflammatoires et antipyrétiques. La catégorie des composés utilisés dans cette méthode de traitement est représentée par la formule (I).