2-(4-Dimethylamino-phenyl)-7-methyl-1H-benzoimidazol-4-ol | 110191-52-1

• 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: 2-(4-Dimethylamino-phenyl)-7-methyl-1H-benzoimidazol-4-ol
• 英文别名: 2-[4-(dimethylamino)phenyl]-7-methyl-3H-benzimidazol-4-ol
• CAS: 110191-52-1
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: CXAFEQGNCLGOSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(benzyloxy)-6-methyl-1,2-phenylenediamine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 xylene 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 2-(4-Dimethylamino-phenyl)-7-methyl-1H-benzoimidazol-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

• 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.