3-(4-methylsulfonylphenyl)-4-(4-fluorophenyl)-thiophene | 157671-69-7

• 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: 3-(4-methylsulfonylphenyl)-4-(4-fluorophenyl)-thiophene
• 英文别名: 3-(4-methylsulfonylphenyl)-4-(4-fluorophenyl) thiophene；3-(4-methylsulfonylphenyl)-4-(4-fluorophenyl)thiophene；3-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)thiophene
• CAS: 157671-69-7
• 化学式: C₁₇H₁₃FO₂S₂
• 分子量: 332.419
• InChiKey: APTPOHBDWBGOML-UHFFFAOYSA-N

物化性质

• 沸点：
  420.218±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.301±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methylsulfonylphenyl)-4-(4-fluorophenyl)-thiophene 在 sodium hydroxide 、 四氯化钛 、 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 生成 [3-(4-Fluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-thiophen-2-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylthiophenes as selective cox-2 inhibitors. part II: Replacing the heterocycle

  摘要：

  The thiophene ring of DuP 697 was replaced by a variety of heterocycles and the products were tested for their ability to inhibit human Cox-2 and Cox-1, the isozymes of cyclooxygenase.

  DOI：

  10.1016/0960-894x(95)00564-a
• 作为产物：
  描述：

  4-甲硫基苯硼酸 在 Oxone 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 生成 3-(4-methylsulfonylphenyl)-4-(4-fluorophenyl)-thiophene
  参考文献：
  名称：

  Chemistry and pharmacokinetics of diarylthiophenes and terphenyls as selective COX-2 inhibitors

  摘要：

  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

  DOI：

  10.1016/s0960-894x(96)00513-6

文献信息

• Method of preparing sulfmonamides from sulfones
  申请人：G. D. Searle & Co.

  公开号：US05684195A1

  公开（公告）日：1997-11-04

  A one-pot synthesis of sulfonamides from sulfones has been developed. Conversion of sulfones to the corresponding sulfinic acid salts is followed by oxidative-amination to give the sulfonamides.

  已开发出一种从磺酮合成磺胺类化合物的一锅法。将磺酮转化为相应的亚砜酸盐，然后进行氧化胺化反应以得到磺胺类化合物。
• Method of treating skin related conditions
  申请人：G. D. Searle & Co.

  公开号：US06274590B1

  公开（公告）日：2001-08-14

  A class of 3,4-diaryl substituted thiophene, derivatives and analogs thereof, pharmaceutical compositions containing them and methods of using them to treat inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I: wherein Y is S; wherein X is one or two substituents selected from hydrido, halo, lower alkoxycarbonyl and carboxyl; wherein R2 and R3 are independently aryl or heteroaryl; and wherein R2 and R3 are optionally substituted with one or more radicals selected from sulfamyl, alkylsulfonyl, halo, lower alkoxy and lower alkyl; or a pharmaceutically-acceptable salt thereof.

  一种3,4-二芳基取代噻吩类，其衍生物和类似物，包含它们的制药组合物以及使用它们治疗炎症和炎症相关疾病的方法。特别感兴趣的化合物由式I定义：其中Y为S；其中X为从氢基，卤素，低烷氧基羰基和羧基中选择的一个或两个取代基；其中R2和R3分别为芳基或杂环芳基；其中R2和R3可以选择地用来自磺酰胺基，烷基磺酰基，卤素，低烷氧基和低烷基的一个或多个基团取代；或其药学上可接受的盐。
• Heterocyclic aromatic oxazole compounds and use thereof
  申请人：——

  公开号：US20020198244A1

  公开（公告）日：2002-12-26

  A heterocyclic aromatic oxazole compound of the formula (I) 1 wherein Z is an oxygen atom; one of R and R 1 is a group of the formula 2 wherein R 3 is lower alkyl, amino or lower alkylamino, and R 4 , R 5 , R 6 and R 7 are the same or different and each is hydrogen atom, halogen atom, lower alkyl, lower alkoxy, trifluoromethyl, hydroxy or amino, provided that at least one of R 4 , R 5 , R 6 and R 7 is not hydrogen atom, and the other is an optionally substituted cycloalkyl, an optionally substituted heterocyclic group or an optionally substituted aryl; and R 2 is a lower alkyl or a halogenated lower alkyl, and a pharmaceutically acceptable salt thereof. The heterocyclic aromatic oxazole compound and pharmaceutically acceptable salts thereof have antipyretic action, analgesic action, anti-inflammatory action, and particularly, selective inhibitory action on cyclooxygenase-2 (COX-2), and are expected to be useful as anti-inflammatory agents with less side-effects such as digestive tract disorders.

  式(I)中，Z为氧原子；R和R1中的一个为式2的基团，其中R3为低碳基、氨基或低碳基氨基，R4、R5、R6和R7相同或不同，且每个为氢原子、卤素原子、低碳基、低碳氧基、三氟甲基、羟基或氨基，但至少有一个为非氢原子，另一个为可选取代的环烷基、可选取代的杂环基或可选取代的芳基；R2为低碳基或卤代低碳基，以及其药学上可接受的盐。该杂环芳香族噁唑化合物及其药学上可接受的盐具有退热作用、镇痛作用、抗炎作用，特别是对环氧合酶-2 (COX-2)的选择性抑制作用，并有望作为抗炎剂使用，具有较少的消化道副作用。
• 3,4-diaryl thiophenes and analogs thereof having use as anti-inflammatory agents
  申请人：G.D. Searle & Co.

  公开号：US20030013744A1

  公开（公告）日：2003-01-16

  A class of 3,4-diaryl substituted thiophene, furan and pyrrole derivatives and analogs thereof, pharmaceutical compositions containing them and methods of using them to treat inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I: 1 wherein Y is selected from O, S and NR 1 ; wherein R 1 is selected from hydrido and lower alkyl; wherein X is one or two substituent selected from hydrido, halo, lower alkoxycarbonyl and carboxyl; wherein R 2 and R 3 are independently aryl or heteroaryl; and wherein R 2 and R 3 are optionally substituted at a substitutable position with one or more radicals selected from sulfamyl, alkylsulfonyl, halo, lower alkoxy and lower alkyl; or a pharmaceutically-acceptable salt thereof.

  一类3,4-二芳基取代的噻吩、呋喃和吡咯衍生物及其类似物，包括含有它们的制药组合物和使用它们治疗炎症和炎症相关疾病的方法。特别感兴趣的化合物由公式I定义：其中Y选择自O、S和NR1；其中R1选择自氢和较低的烷基；其中X是一个或两个取代基，选择自氢、卤素、较低的烷氧羰基和羧基；其中R2和R3分别为芳基或杂芳基；其中R2和R3在可取代位置上可以选择一个或多个基团进行取代，选择自磺酰胺基、烷基磺酰基、卤素、较低的烷氧基和较低的烷基；或其药学上可接受的盐。
• Fused pyrrole compounds, pharmaceutical agents containing the same, and the use thereof
  申请人：——

  公开号：US20040122002A1

  公开（公告）日：2004-06-24

  The present invention relates to fused pyrrole compounds of the formula 1. 1 in which at least one of the radicals R1, R2, R3 is 4-sulphur-substituted phenyl. These compounds are in particular pyrrolizines, indolizines and heteroanalogues having selective inhibitory action on isoenzyme-2 of prostaglandin H synthase (COX-2). The invention also relates to pharmaceutical compositions which contain these compounds; and the use of these compounds for the treatment of disorders of the rheumatic type.

  本发明涉及式1.1的融合吡咯化合物，其中至少一个基团R1、R2、R3是4-硫代取代苯基。这些化合物特别是吡咯啉、吲哚啉和杂环类似物，具有对前列腺素H合成酶同工酶2的选择性抑制作用。本发明还涉及含有这些化合物的药物组合物；以及使用这些化合物治疗风湿性疾病的方法。