4-(p-Butoxyphenyl)imidazole | 53704-65-7

• 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-(p-Butoxyphenyl)imidazole
• 英文别名: 4-(4-butoxy-phenyl)-1(3)H-imidazole；4-<4'-Butyloxy-phenyl>-imidazol；5-(4-Butoxy-phenyl)-1H-imidazole；5-(4-butoxyphenyl)-1H-imidazole
• CAS: 53704-65-7
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: VSYIEXFPNPTQGT-UHFFFAOYSA-N

物化性质

• 熔点：
  124.5 °C
• 沸点：
  427.6±28.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(p-Butoxyphenyl)imidazole 、 硝酸 以33%的产率得到
  参考文献：
  名称：

  IRADYAN M. A.; TOROSYAN A. G.; MIRZOYAN R. G.; AROYAN A. A., XIMIYA GETEROTSIKL. SOEDIN., 1977, HO

  摘要：

  DOI：
• 作为产物：
  描述：

  4-丁氧基苯甲醛 在 氰化钠 、 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 18.33h， 生成 4-(p-Butoxyphenyl)imidazole
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k

文献信息

• [EN] UREA COMPOUNDS AND THEIR USE AS FAAH ENZYME INHIBITORS<br/>[FR] COMPOSÉS D'URÉE ET LEUR UTILISATION COMME INHIBITEURS DE L'ENZYME FAAH
  申请人：BIAL PORTELA & Cª S A

  公开号：WO2015016728A1

  公开（公告）日：2015-02-05

  A compound having Formula (I): wherein: R1 is selected from hydrogen, halogen, hydroxyl and C1-4 alkoxy; R2 is selected from hydrogen, halogen, hydroxyl and C1-4 alkoxy; R3 is C1-4 alkyl; R4 is aryl which is substituted with a group selected from OSO2NH2, NHCONH2, NHSO2NH2, NHSO2C1-4 alkyl and CONH2; and n is 0 or 1; or a pharmaceutically acceptable salt thereof; provided that the compound is not N-(1-benzylpiperidin-4-yl)-N-methyl-4-(4-(sulfamoylamino)phenyl)-1H-imidazole-1-carboxamide or N-(1-benzylpiperidin-4-yl)-N-methyl-4-(3-(methylsulfonamido)phenyl)-1H-imidazole-1-carboxamide. The compound may be used as an inhibitor of fatty acid amide hydrolase.

  具有以下化学式（I）的化合物：其中：R1从氢、卤素、羟基和C1-4烷氧基中选择；R2从氢、卤素、羟基和C1-4烷氧基中选择；R3是C1-4烷基；R4是芳基，其被从OSO2NH2、NHCONH2、NHSO2NH2、NHSO2C1-4烷基和CONH2中选择的基团取代；n为0或1；或其药学上可接受的盐；前提是该化合物不是N-(1-苄基哌啶-4-基)-N-甲基-4-(4-(磺胺氨基)苯基)-1H-咪唑-1-羧酰胺或N-(1-苄基哌啶-4-基)-N-甲基-4-(3-(甲磺酰氨基)苯基)-1H-咪唑-1-羧酰胺。该化合物可用作脂肪酸酰胺水解酶的抑制剂。
• Urea Compounds and Their Use as FAAH Enzyme Inhibitors
  申请人：BIAL-PORTELA & Cª, S.A.

  公开号：US20160166560A1

  公开（公告）日：2016-06-16

  A compound having Formula I: wherein: R1 is selected from hydrogen, halogen, hydroxyl and C 1-4 alkoxy; R2 is selected from hydrogen, halogen, hydroxyl and C 1-4 alkoxy; R3 is C 1-4 alkyl; R4 is aryl which is substituted with a group selected from OSO 2 NH 2 , NHCONH 2 , NHSO 2 NH 2 , NHSO 2 C 1-4 alkyl and CONH 2 ; and n is 0 or 1; or a pharmaceutically acceptable salt thereof; provided that the compound is not N-(1-benzylpiperidin-4-yl)-N-methyl-4-(4-(sulfamoylamino)phenyl)-1H-imidazole-1-carboxamide or N-(1-benzylpiperidin-4-yl)-N-methyl-4-(3-(methyl sulfonamido)phenyl)-1H-imidazole-1-carboxamide. The compound may be used as an inhibitor of fatty acid amide hydrolase.

  化合物I的化学式为：其中：R1选择自氢、卤素、羟基和C1-4烷氧基；R2选择自氢、卤素、羟基和C1-4烷氧基；R3为C1-4烷基；R4为芳基，其被选择自OSO2NH2、NHCONH2、NHSO2NH2、NHSO2C1-4烷基和CONH2的基团取代；n为0或1；或其药学上可接受的盐；但化合物不是N-(1-苄基哌啶-4-基)-N-甲基-4-(4-(磺酰胺基)苯基)-1H-咪唑-1-羧酰胺或N-(1-苄基哌啶-4-基)-N-甲基-4-(3-(甲基磺酰氨基)苯基)-1H-咪唑-1-羧酰胺。该化合物可用作脂肪酸酰胺水解酶的抑制剂。
• METHODS OF MODULATING CELL PROLIFERATION AND CYST FORMATION IN POLYCYSTIC KIDNEY AND LIVER DISEASES
  申请人：The Medical College of Wisconsin, Inc.

  公开号：EP2061450B1

  公开（公告）日：2017-04-19
• Methods of modulating cell proliferation and cyst formation in polycystic kidney and liver diseases
  申请人：Sweeney William E.

  公开号：US20080167382A1

  公开（公告）日：2008-07-10

  The present invention provides a method for preferentially reducing the proliferation of cystic epithelial cells in the kidney or bile duct in a mammal in need thereof by administering a 20-HETE synthesizing enzyme inhibitor or a 20-HETE antagonist to the mammal in an amount sufficient to preferentially reduce the proliferation of cystic epithelial cells over normal epithelial cells such as tubule epithelial cells in the kidney or bile duct. The present invention also provides a method for preventing or treating autosomal dominant polycystic kidney disease (ADPKD), autosomal recessive polycystic kidney disease (ARPKD), ARPKD associated congenital hepatic fibrosis, ARPKD associated Caroli's disease, or cholangiocarcinoma in a mammal in need thereof by administering a 20-HETE synthesizing enzyme inhibitor or a 20-HETE antagonist to the mammal in an amount sufficient to prevent or treat the disease.
• Methods of Modulating Cell Proliferation and Cyst Formation in Polycystic Kidney and Liver Diseases
  申请人：Sweeney William E.

  公开号：US20140329811A1

  公开（公告）日：2014-11-06

  The present invention provides a method for preferentially reducing the proliferation of cystic epithelial cells in the kidney or bile duct in a mammal in need thereof by administering a 20-HETE synthesizing enzyme inhibitor or a 20-HETE antagonist to the mammal in an amount sufficient to preferentially reduce the proliferation of cystic epithelial cells over normal epithelial cells such as tubule epithelial cells in the kidney or bile duct. The present invention also provides a method for preventing or treating autosomal dominant polycystic kidney disease (ADPKD), autosomal recessive polycystic kidney disease (ARPKD), ARPKD associated congenital hepatic fibrosis, ARPKD associated Caroli's disease, or cholangiocarcinoma in a mammal in need thereof by administering a 20-HETE synthesizing enzyme inhibitor or a 20-HETE antagonist to the mammal in an amount sufficient to prevent or treat the disease.