2-(4-甲氧基苄基)-7-甲基-1H-苯并咪唑-4-醇 | 103059-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(4-甲氧基苄基)-7-甲基-1H-苯并咪唑-4-醇
• 英文名称: 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol
• 英文别名: 2-[(4-methoxyphenyl)methyl]-7-methyl-3H-benzimidazol-4-ol
• CAS: 103059-43-4
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: XXQVKKOKMHLULS-UHFFFAOYSA-N

物化性质

• 沸点：
  555.8±45.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.1
• 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 为溶剂， 25.0~130.0 ℃ 、101.33 kPa 条件下， 生成 2-(4-甲氧基苄基)-7-甲基-1H-苯并咪唑-4-醇
  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

• FUSED HETEROCYCLIC COMPOUNDS
  申请人：Aso Kazuyoshi

  公开号：US20100048658A1

  公开（公告）日：2010-02-25

  There is provided a compound of the formula: wherein R 1 is an optionally substituted hydrocarbyl, a substituted amino, etc.; R 2 is an aromatic group substituted with one or two substituents at the positions adjacent to the position bonded to Z, and said aromatic group may have additional substituent(s); X is —NR 3 — wherein R 3 is a hydrogen, an optionally substituted hydrocarbyl or an acyl, or sulfur; Y 1 , Y 2 and Y 3 are an optionally substituted methine or a nitrogen, etc.; and Z is an optionally substituted methylene, provided that carbonyl is excluded; or a salt thereof or a prodrug thereof, which have CRF receptor antagonist activity and use thereof.

  提供了一种化合物，其化学式为：其中，R1为可选取代的烃基、取代氨基等；R2为带有一个或两个取代基的芳基，所述取代基位于与Z键合的位置相邻的位置，并且所述芳基可以具有附加的取代基；X为—NR3—，其中R3为氢、可选取代的烃基或酰基，或硫；Y1、Y2和Y3为可选取代的亚甲基或氮等；Z为可选取代的亚甲基，但不包括羰基；或其盐或前药，具有CRF受体拮抗活性并且可用于治疗。
• US8039500B2
  申请人：——

  公开号：US8039500B2

  公开（公告）日：2011-10-18
• 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.