2-(4-chlorophenyl)-4-[(2-methylphenylthio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-4-[(2-methylphenylthio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole
• 英文别名: 2-(4-Chlorophenyl)-4-[[(2-methylphenyl)thio]methyl]-1-[4-(methylsulfonyl)phenyl]-1h-imidazole；2-(4-chlorophenyl)-4-[(2-methylphenyl)sulfanylmethyl]-1-(4-methylsulfonylphenyl)imidazole
• 化学式: C₂₄H₂₁ClN₂O₂S₂
• 分子量: 469.028
• InChiKey: LKFDEOAVJPOKJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-chloromethyl-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole 、 2-巯基甲苯 在 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 生成 2-(4-chlorophenyl)-4-[(2-methylphenylthio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole
  参考文献：
  名称：

  A process for the preparation of 4-¬2-(aryl or heterocyclo)-1H-imidazol-1-yl|benzenesulfonamides

  摘要：

  公开号：

  EP1193265B1

文献信息

• Heterocyclo-substituted imidazoles for the treatment of inflammation
  申请人：Khanna K. Ish

  公开号：US20050096368A1

  公开（公告）日：2005-05-05

  A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (V), wherein R 3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy. aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R 4 is a radical selected from hydrido, alkyl and halo; and wherein R 13 and R 14 are independently selected from aryl and heterocyclo, wherein R 13 and R 14 are optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro; provided at least one of R 13 and R 14 is aryl substituted with alkylsulfonyl or aminosulfonyl; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物用于治疗炎症。特别感兴趣的化合物由公式（V）定义，其中R3是从氢基，烷基，卤代烷基，芳基烷基，杂环烷基，杂环芳基烷基，酰基，氰基，烷氧基，烷硫基，烷硫基烷基，烷基磺酰基，环烷硫基，环烷硫基烷基，环烷磺酰基，环烷磺酰基烷基，卤代烷基磺酰基，芳基磺酰基，卤代基，羟基烷基，烷氧基烷基，烷基羧酰基，芳基羧酰基，芳基烷基羧酰基，杂环羧酰基，氰基烷基，氨基烷基，烷基氨基烷基，N-芳基氨基烷基，N-烷基-N-芳基氨基烷基，羧基烷基，烷氧基羧酰基烷基，烷氧基羧酰基，卤代烷基羧酰基，羧基，氨基羧酰基，烷基氨基羧酰基，杂环芳基烷氧基烷基，杂环芳基氧基烷基，杂环芳基硫基烷基，芳基硫醇基烷基，芳基氧基烷基，芳基硫醇基，芳基氧基。芳基烷硫基烷基，芳基烷氧基烷基，芳基和杂环芳基;其中R4是从氢基，烷基和卤代基中选择的基团;并且R13和R14分别从芳基和杂环芳基中选择，其中R13和R14在可取代位置上可以选择一个或多个基团独立地选择，包括烷基磺酰基，氨基磺酰基，卤代基，烷硫基，烷基，氰基，羧基，烷氧基羧酰基，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，芳基氨基和硝基; 提供至少一个R13和R14被烷基磺酰基或氨基磺酰基取代的芳基，或其药学上可接受的盐。
• A process for the preparation of 4-[2-(aryl or heterocyclo)-1H-imidazol-1-yl]benzenesulfonamides
  申请人：G.D. Searle & Co.

  公开号：EP1193265A2

  公开（公告）日：2002-04-03

  A process to make a compound of the formula or a pharmaceutically acceptable salt thereof is disclosed wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkaxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R4 is a radical selected from hydrido, alkyl and halo; and wherein R2 is selected from aryl and heterocyclo, wherein R2 is optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro;    said method comprising the steps of forming a (protected sulfonyl)benzenamine, treating said (protected sulfonyl)benzenamine first with a base and then with a nitrile to form an amidine, treating said amidine with a haloketone derivative in the presence of a base to form a hydroxyimidazole, forming a (protected sulfonylphenyl) imidazole by dehydrating said hydroxyimidazole, and forming said compounds by deprotecting said (protected sulfonylphenyl)imidazole.

  本发明公开了一种制备式 或其药学上可接受的盐的工艺。 其中 R3 是选自氢基、烷基、卤代烷基、芳基、杂环烷基、杂芳基、酰基、氰基、烷氧基、烷硫基、烷硫基、烷基磺酰基、环烷硫基、环烷硫基、环烷基磺酰基、环烷基磺酰基、卤代烷基磺酰基、芳基磺酰基、卤代烷基磺酰基、卤代芳基磺酰基、卤代芳基磺酰基、环烷基磺酰基、卤代烷基磺酰基、芳基磺酰基、卤代、羟基烷基、烷氧基烷基、烷基羰基、芳基羰基、芳基羰基、杂环羰基、氰基烷基、氨基烷基、烷基氨基烷基、N-芳基氨基烷基、N-烷基-N-芳基氨基烷基、羧基、烷氧基羰基、烷氧羰基、卤代烷基羰基、羧基、氨基羰基、烷基氨基羰基、烷基氨基羰基烷基、杂芳基烷氧基烷基、杂芳氧基烷基、杂芳硫基烷基、杂芳基硫代烷基、杂芳基硫代烷基、杂芳基氧基烷基、杂芳基硫代烷基、芳基硫代烷基、芳基氧基烷基、芳基硫代烷基、芳基氧基烷基、芳基硫代烷基、芳基烷氧基烷基、芳基和杂芳基；其中 R4 是选自氢基、烷基和卤代的基团；以及 其中 R2 选自芳基和杂环基，其中 R2 在可取代的位置上任选被一个或多个独立选自烷基磺酰基、氨基磺酰基、卤代基、烷硫基、烷基、氰基、羧基、烷氧基羰基、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、芳基氨基和硝基的基团取代； 所述方法包括以下步骤：形成(受保护的磺酰基)苯胺，首先用碱处理所述(受保护的磺酰基)苯胺，然后用腈处理以形成脒，在碱存在下用卤代酮衍生物处理所述脒以形成羟基咪唑，通过使所述羟基咪唑脱水形成(受保护的磺酰基苯基)咪唑，以及通过对所述(受保护的磺酰基苯基)咪唑进行脱保护形成所述化合物。
• [EN] HETEROCYCLO-SUBSTITUTED IMIDAZOLES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] IMIDAZOLES A SUBSTITUTION HETEROCYCLO UTILISES POUR TRAITER L'INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：WO1997027181A1

  公开（公告）日：1997-07-31

  (EN) A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (V), wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R4 is a radical selected from hydrido, alkyl and halo; and wherein R13 and R14 are independently selected from aryl and heterocyclo, wherein R13 and R14 are optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro; provided at least one of R13 and R14 is aryl substituted with alkylsulfonyl or aminosulfonyl; or a pharmaceutically-acceptable salt thereof.(FR) Cette invention concerne une classe de composés d'imidazolyle destinés à être utilisés pour traiter l'inflammation. Des composés particulièrement intéressants sont définis par la formule générale (V). Dans la formule R3 représente un radical sélectionné entre hybrido, alkyle, haloalkyle, aralkyle, hétérocycloalkyle, hétéroaralkyle, acyl, cyano, alkoxy, alkylthio, alkylthioalkyle, alkylsulfonyle, cycloalkylthio, cycloalkylthioalkyle, cycloalkylsulfonyle, cycloalkylsulfonylalkyle, haloalkylsulfonyle, arylsulfonyle, halo, hydroxyalkyle, alcoxyalkyle, alkylcarbonyle, arylcarbonyle, aralkylcarbonyle, hétérocyclocarbonyle, cyanoalkyle, aminoalkyle, alkylaminoalkyle, N-arylaminoalkyle, N-alkyl-N-arylaminoalkyle, carboxyalkyle, alkoxycarbonylalkyle, alkoxycarbonyle, haloalkylcarbonyle, carboxyle, aminocarbonyle, alkylaminocarbonyle, alkylaminocarbonylalkyle, hétéroarylalkoxyalkyle, hétéroaryloxyalkyle, hétéroarylthioalkyle, aralcoxy, aralkylthio, hétéroaralcoxy, hétéroaralkylthio, hétéroarylalkylthioalkyle, hétéroaryloxy, hétéroarylthio, arylthioalkyle, aryloxyalkyle, arylthio, aryloxy, aralkylthioalkyle, aralcoxyalkyle, aryle et hétéroaryle; R4 représente un radical sélectionné entre hybrido, alkyle et halo; R13 and R14 sont indépendamment sélectionnées entre aryle et hétérocyclo, R13 et R14 sont facultativement substitués à une position substituable à un ou plusieurs radicaux sélectionnés indépendamment entre alkylsulfonyle, aminosulfonyle, halo, alkylthio, alkyle, cyano, carboxyle, alkoxycarbonyle, haloalkyle, hydroxyle, alcoxy, hydroxyalkyle, alcoxyalkyle, haloalcoxy, amino, alkylamino, arylamino et nitro; à condition qu'au moins un des éléments R13 et R14 représente aryle remplacé par alkylsulfonyle ou aminosulfonyle ou bien un sel pharmaceutiquement acceptable de ces derniers.

  描述了一类咪唑基化合物，用于治疗炎症。特别感兴趣的化合物由通式(V)定义，其中R3为选自氢代、烷基、卤代烷基、芳烷基、杂环烷基、杂芳烷基、酰基、氰基、烷氧基、烷硫基、烷硫基烷基、烷基磺酰基、环烷基硫基、环烷基硫基烷基、环烷基磺酰基、环烷基磺酰基烷基、卤代烷基磺酰基、芳基磺酰基、卤素、羟基烷基、烷氧基烷基、烷基羰基、芳基羰基、芳烷基羰基、杂环羰基、氰基烷基、氨基烷基、烷基氨基烷基、N-芳基氨基烷基、N-烷基-N-芳基氨基烷基、羧基烷基、烷氧羰基烷基、烷氧羰基、卤代烷基羰基、羧基、氨基羰基、烷基氨基羰基、烷基氨基羰基烷基、杂芳基烷氧基烷基、杂芳基氧基烷基、杂芳基硫基烷基、芳烷氧基、芳烷基硫基、杂芳烷氧基、杂芳烷基硫基、杂芳基烷基硫基烷基、杂芳基氧基、杂芳基硫基、芳基硫基烷基、芳基氧基烷基、芳基硫基、芳基氧基、芳烷基硫基烷基、芳烷氧基烷基、芳基和杂芳基；其中R4为选自氢代、烷基和卤素的基团；并且R13和R14独立地选自芳基和杂环基，其中R13和R14可在一个可被取代的位置上被一个或多个基团取代，这些基团独立地选自烷基磺酰基、氨基磺酰基、卤素、烷硫基、烷基、氰基、羧基、烷氧羰基、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、芳基氨基和硝基；前提是至少一个R13或R14为被烷基磺酰基或氨基磺酰基取代的芳基；或者其药学上可接受的盐。
• 1,2-SUBSTITUTED IMIDAZOLYL COMPOUNDS FOR THE TREATMENT OF INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：EP0772600B1

  公开（公告）日：2002-09-18
• HETEROCYCLO-SUBSTITUTED IMIDAZOLES FOR THE TREATMENT OF INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：EP0880504A1

  公开（公告）日：1998-12-02