1-[4-(benzyloxy)phenethyl]-1H-imidazole | 80199-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[4-(benzyloxy)phenethyl]-1H-imidazole
• 英文别名: 1-{2-[4-(Benzyloxy)phenyl]ethyl}-1H-imidazole；1-[2-(4-phenylmethoxyphenyl)ethyl]imidazole
• CAS: 80199-93-5
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: ZGPCRMIIWBZNGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(benzyloxy)phenethyl]-1H-imidazole 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 18.58h， 生成 1-[4-[2-(1-imidazolyl)ethyl]phenoxy]-3-isopropylamino-2-propanol
  参考文献：
  名称：

  .beta.1-Selective adrenoceptor antagonists. 3. 4-Azolyl linked phenoxypropanolamines

  摘要：

  A series of 4-substituted phenoxypropanolamines has been prepared and examined for beta-adrenoceptor activity. The 4-substituents, di- and triazole ring systems connected to the phenoxy ring by different length chains, were chosen as a means of introducing cardioselectivity. This has been achieved, especially in the 1-[4-[(4-chloropyrazol-1-yl)methoxy] phenoxy]-3-(isopropylamino)-2-propanol (11), the 4-[(2H-1,2,3-triazol-2-yl)methoxy] analogue (21), and the 4-[2-(2H-1,2,3-triazol-2-yl)ethoxy] analogue (22), which show potent beta 1-blockade with selectivity ratios in excess of 100:1. Structure-activity relationships are discussed, and the optimum position of the heteroatom in the 4-substituent is defined.

  DOI：

  10.1021/jm00370a012
• 作为产物：
  描述：

  咪唑 、 1-(2-溴乙基)-4-(苯基甲氧基)苯 在 四丁基溴化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 90.0 ℃ 、1.03 MPa 条件下， 反应 0.67h， 以46%的产率得到1-[4-(benzyloxy)phenethyl]-1H-imidazole
  参考文献：
  名称：

  Development of new HO-1 inhibitors by a thorough scaffold-hopping analysis

  摘要：

  HO-1 inhibition is considered a valuable anticancer approach. In fact, up-regulation of HO-1 had been repeatedly reported in many types of human malignancies, and in these clinical cases, poor outcomes are reported. To identify novel HO-1 inhibitors suitable for drug development, a scaffold-hopping strategy calculation was utilized to design novel derivatives. Different parts of the selected molecule were analyzed and the different series of novel compounds were virtually evaluated. The calculation for the linker moiety of the classical HO-1 inhibitors structure led us to compounds 5 and 6. A synthetic pathway for the two molecules was designed and the compounds were synthesized. The biological activity revealed an HO-1 inhibition of 0.9 and 54 mu M\A for molecules 5 and 6 respectively. This study suggested that our scaffold-hopping approach was successful and these results are ongoing for further development.

  DOI：

  10.1016/j.bioorg.2018.08.023