2-(4-氟苯基)-1-[4-(甲硫基)苯基]-4,4,4-三氟-1,3-丁二酮 | 165252-27-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(4-氟苯基)-1-[4-(甲硫基)苯基]-4,4,4-三氟-1,3-丁二酮
• 英文名称: 2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butanedione
• 英文别名: 2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butandione；4,4,4-trifluoro-2-(4-fluorophenyl)-1-(4-methylsulfanylphenyl)butane-1,3-dione
• CAS: 165252-27-7
• 化学式: C₁₇H₁₂F₄O₂S
• 分子量: 356.341
• InChiKey: OSTLZNCMRREFSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-氟苯基)-1-[4-(甲硫基)苯基]-4,4,4-三氟-1,3-丁二酮 在 Oxone 、 肼 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole
  参考文献：
  名称：

  3,4-diarylpyrazoles: Potent and selective inhibitors of cyclooxygenase-2

  摘要：

  A series of 3,4-diarylpyrazoles was synthesized and evaluated for their ability to selectively inhibit cyclooxygenase-2 (COX-2). A number of potent and selective inhibitors were identified and found to have oral anti-inflammatory activity in a rat carrageenan-induced foot pad edema assay. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00372-7
• 作为产物：
  描述：

  4-氟苯乙酸 在 lithium hexamethyldisilazane 作用下， 生成 2-(4-氟苯基)-1-[4-(甲硫基)苯基]-4,4,4-三氟-1,3-丁二酮
  参考文献：
  名称：

  3,4-diarylpyrazoles: Potent and selective inhibitors of cyclooxygenase-2

  摘要：

  A series of 3,4-diarylpyrazoles was synthesized and evaluated for their ability to selectively inhibit cyclooxygenase-2 (COX-2). A number of potent and selective inhibitors were identified and found to have oral anti-inflammatory activity in a rat carrageenan-induced foot pad edema assay. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00372-7

文献信息

• 1,4,5-triphenyl pyrazolyl compounds for the treatment of inflammation
  申请人：Searle; G. D.

  公开号：US05401765A1

  公开（公告）日：1995-03-28

  A class of 1,4,5-triphenyl pyrazoles is described for the treatment of inflammation, including treatment of pain and disorders such as arthritis. Compounds of particular interest are of Formula I ##STR1## wherein R.sup.1 is one or more groups independently selected from hydrido, methyl, ethyl, methoxy, ethoxy, methylthio, methylsulfinyl, methylsulfonyl, hydroxy, nitro, amino, N-methylamino, acetamido, trifluoromethyl, bromo, iodo, fluoro and chloro; wherein R.sup.2 is selected from hydrido, methyl, ethyl, cyano, trifluoromethyl, difluorochloromethyl, difluoromethyl, pentafluoroethyl and heptafluoropropyl; wherein R.sup.3 is one or more groups independently selected from hydrido, methyl, ethyl, methoxy, ethoxy, methylthio, methylsulfinyl, methylsulfonyl, hydroxy, nitro, amino, N-methylamino, acetamido, trifluoromethyl, bromo, iodo, fluoro and chloro; and wherein R.sup.4 is methyl; or a pharmaceutically-acceptable salt thereof.

  一种1,4,5-三苯基吡唑类化合物被描述用于治疗炎症，包括治疗疼痛和关节炎等疾病。特别感兴趣的化合物属于以下式I ##STR1## 其中R.sup.1是一个或多个独立选择自氢、甲基、乙基、甲氧基、乙氧基、甲硫基、甲砜基、甲砜酰基、羟基、硝基、氨基、N-甲基氨基、乙酰氨基、三氟甲基、溴、碘、氟和氯的基团；其中R.sup.2选择自氢、甲基、乙基、氰基、三氟甲基、二氟氯甲基、二氟甲基、五氟乙基和七氟丙基；其中R.sup.3是一个或多个独立选择自氢、甲基、乙基、甲氧基、乙氧基、甲硫基、甲砜基、甲砜酰基、羟基、硝基、氨基、N-甲基氨基、乙酰氨基、三氟甲基、溴、碘、氟和氯的基团；以及R.sup.4是甲基；或其药用可接受盐。
• 3,4-substituted pyrazoles for the treatment of inflammation
  申请人：G. D. Searle & Co.

  公开号：US05486534A1

  公开（公告）日：1996-01-23

  A class of pyrazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, alkenyl, aralkyl, alkynyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl, arylaminocarbonylalkyl, heterocyclicalkyl, and alkoxycarbonylalkyl; wherein R.sup.3 is aryl substituted at a substitutable position with halo; wherein R.sup.4 is selected from hydrido and haloalkyl; and wherein R.sup.5 is selected from alkyl and amino; or a pharmaceutically-acceptable salt or prodrug thereof.

  描述了一类吡唑基化合物，用于治疗炎症和炎症相关疾病。特别感兴趣的化合物由公式II定义：##STR1##其中R.sup.1从氢基，烷基，烯基，芳基烷基，炔基，氰基烷基，羧基烷基，氨基甲酰基烷基，芳基氨基甲酰基烷基，杂环基烷基和烷氧基烷基中选择；其中R.sup.3在可取代位置处被卤素取代的芳基；其中R.sup.4从氢基和卤代烷基中选择；其中R.sup.5从烷基和氨基中选择；或其药学上可接受的盐或前药。
• Substituted pyrazoles for the treatment of inflammation
  申请人：G. D. Searle & Co.

  公开号：US05580985A1

  公开（公告）日：1996-12-03

  A class of pyrazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, alkenyl, aralkyl, alkynyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl, arylaminocarbonylalkyl, heterocyciicalkyl, and alkoxycarbonylalkyl; wherein R.sup.3 is aryl substituted at a substitutable position with halo; wherein R.sup.4 is selected from hydrido and haloalkyl; and wherein R.sup.5 is selected from alkyl and amino; or a pharmaceutically-acceptable salt or prodrug thereof.

  描述了一类吡唑基化合物，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：##STR1##其中R.sup.1选自氢，烷基，烯基，芳基烷基，炔基，氰基烷基，羧基烷基，氨基甲酰基烷基，芳基氨基甲酰基烷基，杂环基烷基和烷氧基羧基烷基；其中R.sup.3为芳基，在可替换位置上被卤素取代；其中R.sup.4选自氢和卤代烷基；其中R.sup.5选自烷基和氨基；或其药学上可接受的盐或前药。
• 3,4 - substituted pyrazoles for the treatment of inflammation
  申请人：G.D. SEARLE & CO.

  公开号：EP1127878A1

  公开（公告）日：2001-08-29

  A class of pyrazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: wherein R1 is selected from alkyl, aralkyl, alkynyl, cyanoalkyl, carboxyalkyl, aminocarbonylalkyl, arylaminocarbonylalkyl, heterocyclicalkyl, and alkoxycarbonylalkyl; wherein R3 is aryl optionally substituted at a substitutable position with one or more radicals independently selected from halo, alkylthio, alkylsulfinyl, alkyl, cyano, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, N-alkyl-N-arylaminocarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino, heterocyclo and nitro; wherein R4 is haloalkyl; and wherein R5 is selected from alkyl and amino; 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吡唑化合物。特别感兴趣的化合物由式 II： 其中 R1 选自烷基、芳烷基、炔基、氰基烷基、羧基烷基、氨基羰基烷基、芳基氨基羰基烷基、杂环烷基和烷氧基羰基烷基；其中 R3 是芳基，可任选地被一个或多个独立选自卤代、烷硫基、烷亚磺酰基、烷基、氰基、羧基、烷氧基羰基、氨基羰基、烷基氨基羰基、芳基氨基羰基、N-烷基-N-芳基氨基羰基、卤代烷基、羟基、烷氧基、羟基烷基、烷氧基烷基、卤代烷氧基、氨基、烷基氨基、芳基氨基、杂环烷基和硝基的基团取代；其中 R4 为卤代烷基；R5 选自烷基和氨基；或其药学上可接受的盐。
• [EN] 1,4,5-TRIPHENYL PYRAZOLYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION AND INFLAMMATION-RELATED DISORDERS<br/>[FR] COMPOSES DU 1,4,5-TRIPHENYLE PYRAZOLYLE DESTINES AU TRAITEMENT DES INFLAMMATIONS ET DES TROUBLES LIES AUX INFLAMMATIONS
  申请人：G.D. SEARLE & CO.

  公开号：WO1995015317A1

  公开（公告）日：1995-06-08

  (EN) A class of 1,4,5-triphenyl pyrazoles is described for the treatment of inflammation, including treatment of pain and disorders such as arthritis. Compounds of particular interest are of formula (II), wherein R1 is selected from the group hydrido, halo, alkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, amino, N-monoalkylamino, N,N-dialkylamino, acylamino, acylaminoalkyl, haloalkyl, hydroxy and alkoxy; wherein R2 is selected from hydrido, alkyl, cyano and haloalkyl; wherein R3 is selected from the group hydrido, halo, alkyl, alkylthio, alkylsulfinyl, alkylsufonyl, nitro, amino, N-monoalkylamino, N,N-dialkylamino, acylamino, acylaminoalkyl, haloalkyl, hydroxy and alkoxy; and wherein R4 is alkyl or amino; or a pharmaceutically-acceptable salt thereof.(FR) La présente invention concerne une classe de 1,4,5-triphényle pyrazoles destinés au traitement des inflammations, y compris le traitement des douleurs et troubles tels que l'arthrite. Les composés présentant un intérêt tout particulier sont conformes à la formule générale (II), où R1 est sélectionné dans le groupe hydrido, halo, alkyle, alkylthio, alkylsulfinyle, alkylsulfonyle, nitro, amino, N-monoalkylamino, N,N-dialkylamino, acylamino, acylaminoalkyle, haloalkyle, hydroxy et alcoxy; où R2 est sélectionné dans le groupe hydrido, alkyle, cyano et aloalkyle; où R3 est sélectionné dans le groupe hydrido, halo, alkyle, alkylthio, alkylsulfinyle, alkylsulfonyle, nitro, amino, N-monoalkylamino, N,N-dialkylamino, acylamino, acylaminoalkyle, haloalkyle, hydroxy et alcoxy; et où R4 est alkyle ou amino; ou un des ses sels compatibles sur le plan pharmaceutique.

  以下是一段英文文本的中文翻译： *(EN) 一种1,4,5-三苯杂二噁唑类化合物的类群被描述为用于治疗炎症，包括治疗痛觉和类风湿关节炎等炎症性疾病。特别感兴趣的是以下化合物的公式(II)，其中R1被选自hydrido、halo、alkyl、alkylthio、alkylsulfinyl、alkylsulfonyl、nitro、amino、N-monoalkylamino、N,N-dialkylamino、acylamino、acylamino-alkyl、haloalkyl、hydroxy和alkoxy；R2被选自hydrido、alkyl、cyano和haloalkyl；R3被选自hydrido、halo、alkyl、alkylthio、alkylsulfinyl、alkylsulfonyl、nitro、amino、N-monoalkylamino、N,N-dialkylamino、acylamino、acylamino-alkyl、haloalkyl、hydroxy和alkoxy；而R4为甲基或氨基；或其 pharmaceutically-acceptable 盐。*(FR) 本发明涉及一类 1,4,5-三苯杂二噁唑化合物，用于炎症治疗，包括治疗疼痛和类风湿关节炎等相关炎症性疾病。特别值得注意的是，符合以下一般式（II）的化合物，其中，R1被选自hydrido、halo、alkyl、alkylthio、alkylsulfinyl、alkylsulfonyl、nitro、amino、 N-monoalkylamino、N,N-dialkylamino、acylamino、acylamino-alkyl、haloalkyl、hydroxy和alkoxy；R2被选自hydrido、alkyl、cyano和haloalkyl；R3被选自hydrido、halo、alkyl、alkylthio、alkylsulfinyl、alkylsulfonyl、nitro、amino、 N-monoalkylamino、N,N-dialkylamino、acylamino、acylamino-alkyl、haloalkyl、hydroxy和alkoxy；其中，R4为甲基或氨基；或其 pharmaceutically-acceptable 盐。