5-[(4-methylsulfonyl)phenyl]-4-(2-fluorophenyl)-2-(2-chlorophenyl)thiazole

• 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: 5-[(4-methylsulfonyl)phenyl]-4-(2-fluorophenyl)-2-(2-chlorophenyl)thiazole
• 英文别名: 2-(2-Chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole；2-(2-Chloro-phenyl)-4-(2-fluoro-phenyl)-5-(4-methanesulfonyl-phenyl)-thiazole；2-(2-chlorophenyl)-4-(2-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole
• 化学式: C₂₂H₁₅ClFNO₂S₂
• 分子量: 443.95
• InChiKey: JOAVZZKMDXSPHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯硫代苯甲酰胺 在 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 生成 5-[(4-methylsulfonyl)phenyl]-4-(2-fluorophenyl)-2-(2-chlorophenyl)thiazole
  参考文献：
  名称：

  Design and synthesis of sulfonyl-substituted 4,5-diarylthiazoles as selective cyclooxygenase-2 inhibitors

  摘要：

  A series of novel sulfone substituted 4,5-diarylthiazoles have been synthesized and evaluated for their inhibition of the two isoforms of human cyclooxygenase (COX-1 and COX-2). This series displays exceptionally selective COX-2 inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00158-4

文献信息

• Substituted thiazoles for the treatment of inflammation
  申请人：G.D. Searle & Co.

  公开号：US05668161A1

  公开（公告）日：1997-09-16

  A class of substituted thiazolyl compounds is described for use in treating inflammation disorders. Compounds are defined by Formula II ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, haloalkyl, cyanoalkyl, alkylamino, aralkyl, arylamino, heteroarylsulfonylalkyl, heteroarylsulfonylhaloalkyl, aralkylamino, aryloxyalkyl, alkoxycarbonyl, aryl optionally substituted at a substitutable position with one or more radicals selected from halo and alkoxy, and heterocyclic optionally substituted at a substitutable position with one or more radicals selected from halo and alkyl; wherein R.sup.4 is selected from alkyl and amino; and wherein R.sup.5 is selected from aryl and heteroaryl; wherein R.sup.5 is optionally substituted at a substitutable position with one or more radicals selected from halo, alkyl and alkoxy; provided R.sup.5 is not phenyl at position 4 when R.sup.1 is .alpha.,.alpha.-bis(trifluoromethyl)methanol and R.sup.4 is methyl; or a pharmaceutically-acceptable salt thereof.

  描述了一类取代噻唑基化合物，用于治疗炎症性疾病。这些化合物由公式II定义，其中R.sup.1从氢化物、烷基、卤代烷基、氰基烷基、烷基胺基、芳基烷基、芳基胺基、杂环磺酰基烷基、杂环磺酰基卤代烷基、芳基胺基、芳氧基烷基、烷氧羰基、芳基（在可取代位置上可用一个或多个卤素和烷氧基选择的基团）和杂环（在可取代位置上可用一个或多个卤素和烷基选择的基团）中选择；其中R.sup.4从烷基和氨基中选择；其中R.sup.5从芳基和杂环中选择；其中R.sup.5在可取代位置上可用一个或多个卤素、烷基和烷氧基选择的基团进行取代；只要R.sup.5不是苯基在位置4时，当R.sup.1是α,α-双（三氟甲基）甲醇且R.sup.4是甲基；或其药用可接受盐。
• [EN] SUBSTITUTED THIAZOLES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] THIAZOLES SUBSTITUES DESTINES AU TRAITEMENT DE L'INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：WO1996003392A1

  公开（公告）日：1996-02-08

  (EN) A class of substituted thiazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula (II), wherein R4 is selected from alkyl and amino, wherein R5 is selected from aryl, cycloalkyl, cycloalkenyl and heterocyclic; wherein R5 is optionally substituted at a substitutable position with one or more radicals selected from halo, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aminosulfonyl, alkyl, alkenyl, alkynyl, cyano, carboxyl, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, acyl, N-alkylaminocarbonyl, N-arylaminocarbonyl, N,N-dialkylaminocarbonyl, N-alkyl-N-arylaminocarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, haloalkoxy, amino, N-alkylamino, N,N-dialkylamino, heterocyclic and nitro; and wherein R6 is selected from halo, amino, alkoxy, nitro, hydroxyl, aminocarbonyl, acyl, alkylaminocarbonyl, arylaminocarbonyl, alkenyl, alkynyl, haloalkoxy, alkylamino, arylamino, aralkylamino, alkoxycarbonylalkyl, alkylaminoalkyl, heterocycloalkyl, aralkyl, cyanoalkyl, N-alkylsulfonylamino, heteroarylsulfonylalkyl, heteroarylsulfonylhaloalkyl, aryloxyalkyl, aralkyloxyalkyl, aryl and heterocyclo, wherein the aryl and heterocyclo radicals are optionally substituted at a substitutable position with one or more radicals selected from halo, alkyl, alkoxy, alkylthio, alkylsulfinyl, haloalkyl, haloalkoxy, carboxyalkyl, alkoxycarbonyl, aminocarbonyl, amino, acyl and alkylamino; or a pharmaceutically-acceptable salt thereof.(FR) La présente invention concerne une classe de composés à base de thiazolyle substitué destinés au traitement de l'inflammation et des troubles liés à l'inflammation. Les composés concernés en l'occurrence sont décrits par la formule générale (II). Dans cette formule générale, R4 est choisi parmi alkyle et amino. R5 est choisi parmi aryle, cycloalkyle, cycloalcényle et hétérocyclique. R5 est éventuellement substitué à des positions admettant la substitution par un ou plusieurs radicaux choisis parmi halo, alkylthio, alkylsulfinyle, alkylsulfonyle, haloalkylsulfonyle, aminosulfonyle, alkyle, alcényle, alkynyle, cyano, carboxyle, carboxyalkyle, alcoxycarbonyle, aminocarbonyle, acyle, N-alkylaminocarbonyle, N-arylaminocarbonyle, N,N-dialkylaminocarbonyle, N-alkyl-N-alkylaminocarbonyle, haloalkyle, hydroxyle, alcoxy, hydroxyalkyle, haloalcoxy, amino, N-alkylamino, N,N-dialkylamino, hétérocyclique et nitro. Dans cette formule générale, R6 est choisi parmi halo, amino, alcoxy, nitro, hydroxyle, aminocarbonyle, acyle, alkylaminocarbonyle, arylaminocarbonyle, alcényle, alkynyle, haloalcoxy, alkylamino, arylamino, aralkylamino, alcoxycarbonylalkyle, alkylaminoalkyle, hétérocycloalkyle, aralkyle, cyanoalkyle, N-alkysulfonylamino, hétéroarylsulfonylalkyle, hétéroarylsulfonylhaloalkyle, aryloxyalkyle, aralkyloxyalkyle, aryle et hétérocyclo, où les radicaux aryle et hétérocyclo peuvent être éventuellement substitués à une position admettant la substitution par au moins un radical choisi parmi halo, alkyle, alcoxy, alkylthio, alkylsulfinyle, haloalkyle, haloalcoxy, carboxyalkyle, alcoxycarbonyle, aminocarbonyle, amino, acyle et alkylamino. L'invention concerne également des sels de ces composés de formule générale (II), qui sont pharmaceutiquement acceptables.

  描述了一类取代噻唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由公式（II）定义，其中R4选择自烷基和氨基，其中R5选择自芳基，环烷基，环烯基和杂环；其中R5在可取代的位置上可选择用一个或多个基团进行取代，所述基团选择自卤素，烷硫基，烷基亚砜基，烷基磺酰基，卤代烷基磺酰基，氨基磺酰基，烷基，烯基，炔基，氰基，羧基，羧基烷基，烷氧基羧酸酯基，氨基羧酸酯基，酰基，N-烷基氨基羧酸酯基，N-芳基氨基羧酸酯基，N，N-二烷基氨基羧酸酯基，N-烷基-N-芳基氨基羧酸酯基，卤代烷基，羟基，烷氧基，卤代烷氧基，氨基，N-烷基氨基，N，N-二烷基氨基，杂环和硝基；其中R6选择自卤素，氨基，烷氧基，硝基，羟基，氨基羧酸酯基，酰基，烷基氨基羧酸酯基，芳基氨基羧酸酯基，烯基，炔基，卤代烷氧基，烷基氨基，芳基氨基，芳基烷基氨基，烷氧基羧酸酯基烷基，烷基氨基烷基，杂环环烷基，芳基烷基，卤代基烷基磺酰氨基，杂环芳基磺酰基烷基，杂环芳基磺酰卤代烷基，芳氧基烷基，芳基烷氧基烷基，芳基和杂环，其中芳基和杂环基团在可取代的位置上可选择用一个或多个基团进行取代，所述基团选择自卤素，烷基，烷氧基，烷硫基，烷基亚砜基，卤代烷基，卤代烷氧基，羧基烷基，烷氧基羧酸酯基，氨基羧酸酯基，氨基，酰基和烷基氨基；或其药学上可接受的盐。
• SUBSTITUTED THIAZOLES FOR THE TREATMENT OF INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：EP0772606A1

  公开（公告）日：1997-05-14
• US5668161A
  申请人：——

  公开号：US5668161A

  公开（公告）日：1997-09-16