4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazole | 175676-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazole
• 英文别名: 4-(4-fluorophenyl)-3-(4-methylsulfanylphenyl)-5-(trifluoromethyl)-1H-pyrazole
• CAS: 175676-89-8
• 化学式: C₁₇H₁₂F₄N₂S
• 分子量: 352.355
• InChiKey: NTCZRPUJIGWKOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-5-(trifluoromethyl)-1H-pyrazole 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 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：

  2-(4-fluorophenyl)-1-(4-(methylthio)phenyl)ethanone 在 lithium hexamethyldisilazane 、 肼 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 4-(4-fluorophenyl)-3-[4-(methylthio)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

文献信息

• 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.

  一类吡唑基化合物用于治疗炎症和炎症相关的疾病。特别感兴趣的化合物由式II定义：其中R.sup.1从氢代基、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、杂环烷基和烷氧基甲酰基中选择；其中R.sup.3是芳基，在可取代位置上取代为卤素；其中R.sup.4从氢代基和卤代烷基中选择；其中R.sup.5从烷基和氨基中选择；或其药用可接受的盐或前药。
• 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] 3,4-SUBSTITUTED PYRAZOLES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] PYRAZOLES 3,4-SUBSTITUEES DESTINEES AU TRAITEMENT DES INFLAMMATIONS
  申请人：G.D. SEARLE & CO.

  公开号：WO1996003385A1

  公开（公告）日：1996-02-08

  (EN) 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.(FR) On décrit une classe de composés ou leurs sels pharmacologiquement acceptables, à base de pyrazolyle, utiles pour traiter des inflammations et des troubles en découlant. Les composés présentant un intérêt particulier sont définis par la formule (II), où R1 est choisi parmi alkyle, arakyle, alkynyle, cyanoalkyle, carboxyalkyle, aminocarbonylalkyle, arylaminocarbonylalkyle, alkyle hétérocyclique et alcoxycarbonylalkyle; R3 représente aryle éventuellement substitué en une position substituable avec un ou plusieurs radicaux choisis indépendemment parmi halo, alkylthio, alkylsulfinyle, alkyle, cyano, carboxyle, alcoxycarbonyle, aminocarbonyle, alkylaminocarbonyle, arylaminocarbonyle, N-alkyle-N-arylamonicarbonyle, haloalkyle, hydroxyle, alcoxy, hydroxyalkyle, alcoxyalkyle, haloalcoxy, amino, alkylamino, arylamino, hétérocyclo et nitro; R4 représente haloalkyle, et R5 est choisi entre alkyle et amino.

  描述了一类吡唑基化合物及其药用盐，用于治疗炎症及相关疾病。特别感兴趣的是由式(II)定义的化合物，其中R1选自烷基、芳烷基、炔基、氰基烷基、羧基烷基、氨基甲酰基烷基、芳氨基甲酰基烷基、杂环烷基和烷氧基羰基烷基；R3为芳基，可被一个或多个独立选择的取代基在可取代的位置上取代，这些取代基选自卤素、烷硫基、烷基磺酰基、烷基、氰基、羧基、烷氧基羰基、氨基甲酰基、烷基氨基甲酰基、芳基氨基甲酰基、N-烷基-N-芳基氨基甲酰基、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、杂环基和硝基；R4为卤代烷基；而R5则选自烷基和氨基。
• 3,4-SUBSTITUTED PYRAZOLES FOR THE TREATMENT OF INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：EP0772597B1

  公开（公告）日：2001-12-12