5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol | 108381-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol
• 英文别名: 5-tert-Butyl-4-hydroxy-7-methyl-2-trifluoro-methylbenzimidazole；5-tert-butyl-7-methyl-2-(trifluoromethyl)-3H-benzimidazol-4-ol
• CAS: 108381-56-2
• 化学式: C₁₃H₁₅F₃N₂O
• 分子量: 272.27
• InChiKey: OCQYEFQMKMVZBA-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  363.9±42.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-tert-butyl-2,3-dinitro-4-methylphenol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0~130.0 ℃ 、101.33 kPa 条件下， 生成 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol
  参考文献：
  名称：

  Novel 1H-benzimidazol-4-ols with potent 5-lipoxygenase inhibitory activity

  摘要：

  The synthesis and structure--activity profile of 2-substituted benzimidazol-4-ols as inhibitors of cell-free RBL-1 5-lipoxygenase are discussed, and their potency is compared with that of the standard inhibitors phenidone, AA 861, BW 755C, and nordihydroguaiaretic acid. In contrast to the standard compounds, most did not inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vivo when administered at 200 microM ip to rats subjected to peritoneal anaphylaxis, although five compounds containing a methoxylated benzyl group (compounds 36, 39, 42, and 43) or hydroxylated benzyl group (41) showed similar activity to that of phenidone, nordihydroguaiaretic acid, and AA 861. Of the many compounds tested, two, 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol (57) and 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol (36), like dexamethasone, inhibited monocyte accumulation in a pleural exudate model of inflammation. Standard lipoxygenase inhibitors such as phenidone, BW 755C, and AA 861 were inactive in this system.

  DOI：

  10.1021/jm00395a007

文献信息

• Derivatives of 2-fluoroalkylbenzimidazole, process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0211489A2

  公开（公告）日：1987-02-25

  A compound of the general formula 1: or a salt or solvate thereof, in which, R' represents hydrogen or a lower alkyl group, R2 represents hydrogen, a lower alkyl group, or R3 represents hydrogen, a lower alkyl group, or R4 represents a lower alkyl group substituted by one or more fluorine atoms, R5 represents hydrogen, halogen or lower alkyl, and R6 represents a lower alkyl or a substituted or unsubstituted carbocyclic aryl group.

  通式 1 的化合物：或其盐或溶液，其中，R'代表氢或低级烷基，R2 代表氢、低级烷基，或 R3 代表氢、低级烷基，或 R4 代表被一个或多个氟原子取代的低级烷基，R5 代表氢、卤素或低级烷基，R6 代表低级烷基或取代或未取代的碳环芳基。
• BUCKLE, DEREK R.;FOSTER, KEITH A.;TAYLOR, JOHN F.;TEDDER, JOHN M.;THODY, +, J. MED. CHEM., 30,(1987) N 12, 2216-2221
  作者：BUCKLE, DEREK R.、FOSTER, KEITH A.、TAYLOR, JOHN F.、TEDDER, JOHN M.、THODY, +

  DOI：——

  日期：——
• US4755525A
  申请人：——

  公开号：US4755525A

  公开（公告）日：1988-07-05
• Novel 1H-benzimidazol-4-ols with potent 5-lipoxygenase inhibitory activity
  作者：Derek R. Buckle、Keith A. Foster、John F. Taylor、John M. Tedder、Veronica E. Thody、Richard A. B. Webster、Jose Bermudez、Roger E. Markwell、Stephen A. Smith

  DOI：10.1021/jm00395a007

  日期：1987.12

  The synthesis and structure--activity profile of 2-substituted benzimidazol-4-ols as inhibitors of cell-free RBL-1 5-lipoxygenase are discussed, and their potency is compared with that of the standard inhibitors phenidone, AA 861, BW 755C, and nordihydroguaiaretic acid. In contrast to the standard compounds, most did not inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vivo when administered at 200 microM ip to rats subjected to peritoneal anaphylaxis, although five compounds containing a methoxylated benzyl group (compounds 36, 39, 42, and 43) or hydroxylated benzyl group (41) showed similar activity to that of phenidone, nordihydroguaiaretic acid, and AA 861. Of the many compounds tested, two, 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol (57) and 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol (36), like dexamethasone, inhibited monocyte accumulation in a pleural exudate model of inflammation. Standard lipoxygenase inhibitors such as phenidone, BW 755C, and AA 861 were inactive in this system.