(2-propyl-1H-benzo[d]imidazol-6-yl)methanol | 68740-39-6

• 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-propyl-1H-benzo[d]imidazol-6-yl)methanol
• 英文别名: (2-propyl-1H-benzo[d]imidazol-5-yl)methanol；(2-propyl-3H-benzimidazol-5-yl)methanol
• CAS: 68740-39-6
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: FWOQZRBKEYHZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-propyl-1H-benzo[d]imidazol-6-yl)methanol 、 氯化亚砜 在 丙酮 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以yielding 4.3 parts of 5-(chloromethyl)-2-propyl-1H-benzimidazole monohydrochloride的产率得到5-(chloromethyl)-2-propyl-1H-benzimidazole monohydrochloride
  参考文献：
  名称：

  5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives

  摘要：

  这是一种具有抗过敏和抗组胺作用的新型5-[4-(二芳基甲基)-1-哌嗪基烷基]苯并咪唑衍生物。

  公开号：

  US04179505A1
• 作为产物：
  描述：

  2-propyl-1H-benzo[d]imidazole-5-carboxylic acid 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 以54%的产率得到(2-propyl-1H-benzo[d]imidazol-6-yl)methanol
  参考文献：
  名称：

  Characterization of new PPARγ agonists: Benzimidazole derivatives—importance of positions 5 and 6, and computational studies on the binding mode

  摘要：

  In this and previous studies we investigated the importance of partial structures of Telmisartan on PPAR gamma activation. The biphenyl-4-ylmethyl moiety at N1 and residues at C2 of the central benzimidazole were identified to be essential for receptor activation and potency of receptor binding. Now we focused our attention on positions 5 and 6 of the central benzimidazole and introduced bromine (3b-5/6, 3c), phenylcarbonyl (3d-5/6), hydroxy(phenyl) methyl (3g-5/6), hydroxymethyl (3h-5/6) and formyl (3i) groups. The selection of these moieties was inspired by the structure of Losartan and its metabolite EXP3179. In order to increase the hydrophobicity of the central part of the molecule, the benzimidazole was exchanged by a naphtho[2,3-d] imidazole (5). The compounds 3a-3i and 5 were tested in a differentiation assay using 3T3-L1 preadipocytes and a luciferase assay using COS-7 cells, transiently transfected with pGal4-hPPAR gamma DEF, pGal5-TK-pGL3 and pRL-CMV, as established models for the assessment of cellular PPAR gamma activation. An enhanced effect on PPAR gamma activation could be observed if lipophilic moieties are introduced in these positions. 4 '-[(2-Propyl-1H-naphtho[2,3-d] imidazol-1-yl) methyl] biphenyl-2-carboxylic acid (5) was identified as the most potent compound with an EC50 of 0.26 mu M and the profile of a full agonist.Together with compounds of the former structure-activity relationship study (position 2-substituted benzimidazole derivatives 4a-4j), the binding mode of Telmisartan and its derivatives have been analyzed in 3D pharmacophore-driven docking experiments. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.102

文献信息

• US4179505A
  申请人：——

  公开号：US4179505A

  公开（公告）日：1979-12-18
• US4243806A
  申请人：——

  公开号：US4243806A

  公开（公告）日：1981-01-06
• Characterization of new PPARγ agonists: Benzimidazole derivatives—importance of positions 5 and 6, and computational studies on the binding mode
  作者：Matthias Goebel、Gerhard Wolber、Patrick Markt、Bart Staels、Thomas Unger、Ulrich Kintscher、Ronald Gust

  DOI：10.1016/j.bmc.2010.06.102

  日期：2010.8

  In this and previous studies we investigated the importance of partial structures of Telmisartan on PPAR gamma activation. The biphenyl-4-ylmethyl moiety at N1 and residues at C2 of the central benzimidazole were identified to be essential for receptor activation and potency of receptor binding. Now we focused our attention on positions 5 and 6 of the central benzimidazole and introduced bromine (3b-5/6, 3c), phenylcarbonyl (3d-5/6), hydroxy(phenyl) methyl (3g-5/6), hydroxymethyl (3h-5/6) and formyl (3i) groups. The selection of these moieties was inspired by the structure of Losartan and its metabolite EXP3179. In order to increase the hydrophobicity of the central part of the molecule, the benzimidazole was exchanged by a naphtho[2,3-d] imidazole (5). The compounds 3a-3i and 5 were tested in a differentiation assay using 3T3-L1 preadipocytes and a luciferase assay using COS-7 cells, transiently transfected with pGal4-hPPAR gamma DEF, pGal5-TK-pGL3 and pRL-CMV, as established models for the assessment of cellular PPAR gamma activation. An enhanced effect on PPAR gamma activation could be observed if lipophilic moieties are introduced in these positions. 4 '-[(2-Propyl-1H-naphtho[2,3-d] imidazol-1-yl) methyl] biphenyl-2-carboxylic acid (5) was identified as the most potent compound with an EC50 of 0.26 mu M and the profile of a full agonist.Together with compounds of the former structure-activity relationship study (position 2-substituted benzimidazole derivatives 4a-4j), the binding mode of Telmisartan and its derivatives have been analyzed in 3D pharmacophore-driven docking experiments. (C) 2010 Elsevier Ltd. All rights reserved.
• 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04179505A1

  公开（公告）日：1979-12-18

  Novel 5-[4-(diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives having antiallergic and antihistaminic properties.

  具有抗过敏和抗组胺作用的新型5-[4-(二芳基甲基)-1-哌嗪基烷基]苯并咪唑衍生物。