2-(4-aminosulfonylphenyl)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone | 177561-50-1

• 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-aminosulfonylphenyl)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone
• 英文别名: 4-[1-Bromo-2-(3-fluoro-4-methoxyphenyl)-2-oxoethyl]benzenesulfonamide
• CAS: 177561-50-1
• 化学式: C₁₅H₁₃BrFNO₄S
• 分子量: 402.241
• InChiKey: ZITBWPAMEWGAOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氯硫代苯甲酰胺 、 2-(4-aminosulfonylphenyl)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone 生成 4-[2-(2-chlorophenyl)-4-(3-fluoro-4-methoxyphenyl)-1,3-thiazol-5-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors

  摘要：

  A series of sulfonamide-substituted 4,5-diarylthiazoles was prepared via three synthetic routes as selective COX-2 inhibitors. Recently in the synthesis of selective COX-2 inhibitors we have discovered that the sulfonamide moiety is a suitable replacement for the methylsulfonyl moiety yielding compounds with activity both in vitro and in vivo. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00157-2
• 作为产物：
  描述：

  2-氟苯甲醚 在 氯磺酸 、 ammonium hydroxide 、 三氯化铝 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-(4-aminosulfonylphenyl)-2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors

  摘要：

  A series of sulfonamide-substituted 4,5-diarylthiazoles was prepared via three synthetic routes as selective COX-2 inhibitors. Recently in the synthesis of selective COX-2 inhibitors we have discovered that the sulfonamide moiety is a suitable replacement for the methylsulfonyl moiety yielding compounds with activity both in vitro and in vivo. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00157-2

文献信息

• [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：EP1125932A2

  公开（公告）日：2001-08-22

  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 methyl and amino; wherein R5 is selected from optionally substituted aryl, cycloalkyl, cycloalkenyl and heterocyclic; and wherein R6 is selected from hydrogen or specified substituents; or a pharmaceutically-acceptable salt thereof.

  描述了一类用于治疗炎症和炎症相关疾病的取代噻唑化合物。特别感兴趣的化合物由式 II 定义 其中 R4 选自甲基和氨基；其中 R5 选自任选取代的芳基、环烷基、环烯基和杂环基；其中 R6 选自氢或特定取代基；或其药学上可接受的盐。
• SUBSTITUTED IMIDAZO 1,2A]AZINES AS SELECTIVE INHIBOTORS OF COX-2
  申请人：LABORATORIOS S.A.L.V.A.T., S.A.

  公开号：EP1104762A1

  公开（公告）日：2001-06-06

  The invention refers to new compounds of formula (I), wherein A and B are selected from the group consisting of N and CH, with the condition that when A is N, B is N; R1 is selected from the group consisting of CH3 and NH2; R2 and R3 are selected from the group consisting of H, CH3, Br, Cl, COCH3 and OCH3; and R4, R5 and R6, are selected from the group consisting of H, F, Cl, Br, (C1-C3)-alkyl, trifluoromethyl, (C1-C3)-alkoxy and trifluoromethoxy. Compounds of formula (I) are prepared by reaction of a substituted aminoazine with a substituted 2-bromo-2-(4-R1-sulfonylphenyl)-1-phenylethanone in a polar solvent. These new compounds inhibit COX-2 with high selectivity over COX-1. They are useful for the treatment of inflamation and/or cyclooxygenase-mediated diseases, having the additional advantage of a reduced potencial for ulcerogenic effects.

  本发明涉及式(I)的新化合物，其中A和B选自由N和CH组成的组，条件是当A为N时，B为N；R1选自由CH3和NH2组成的组；R2和R3选自由H、CH3、Br、Cl、COCH3和OCH3组成的组；以及R4、R5和R6选自由H、F、Cl、Br、(C1-C3)-烷基、三氟甲基、(C1-C3)-烷氧基和三氟甲氧基组成的组。式(I)化合物是由取代的氨基嗪与取代的 2-溴-2-(4-R1-砜基苯基)-1-苯乙酮在极性溶剂中反应制备而成。这些新化合物抑制 COX-2 的选择性高于 COX-1。它们可用于治疗炎症和/或环氧合酶介导的疾病，还具有减少致溃疡作用的潜力。
• SUBSTITUTED IMIDAZO[1,2A]AZINES AS SELECTIVE INHIBITORS OF COX-2
  申请人：LABORATORIOS S.A.L.V.A.T., S.A.

  公开号：EP1104762B1

  公开（公告）日：2002-09-18
• 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