2-Imidazol-1-yl-1-(4-phenoxy-phenyl)-ethanone | 73932-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Imidazol-1-yl-1-(4-phenoxy-phenyl)-ethanone
• 英文别名: 2-Imidazol-1-yl-1-(4-phenoxyphenyl)ethanone
• CAS: 73932-05-5
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: DTLBEUTZQKHVFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Imidazol-1-yl-1-(4-phenoxy-phenyl)-ethanone 在 盐酸 、 sodium tetrahydroborate 、 sodium hydride 作用下， 反应 22.0h， 生成 1-[2-Benzyloxy-2-(4-phenoxy-phenyl)-ethyl]-1H-imidazole; hydrochloride
  参考文献：
  名称：

  Tajana; Cappelletti; Leonardi, Arzneimittel Forschung, 1982, vol. 31, # 12, p. 2121 - 2123

  摘要：

  DOI：
• 作为产物：
  描述：

  咪唑 、 2-溴-1-(4-苯氧基苯基)乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-Imidazol-1-yl-1-(4-phenoxy-phenyl)-ethanone
  参考文献：
  名称：

  Potholing of the hydrophobic heme oxygenase-1 western region for the search of potent and selective imidazole-based inhibitors

  摘要：

  Here we report the design, synthesis, and molecular modeling of new potent and selective imidazolebased HO-1 inhibitors in which the imidazole nucleus and the hydrophobic groups are linked by a phenylethanolic spacer. Most of the tested compounds showed a good inhibitor activity with IC50 values in the low micromolar range, with two of them (lb and 1j) exhibiting also high selectivity toward HO-2. These results were obtained by the idea of potholing the entire volume of the principal hydrophobic western region with an appropriate ligand volume. Molecular modeling studies showed that these molecules bind to the HO-1 in the consolidated fashion where the imidazolyl moiety coordinates the heme iron while the aromatic groups are stabilized by hydrophobic interaction in the western region of the binding pocket. Finally, the synthesized compounds were analyzed for in silico ADME-Tox properties to establish oral drug-like behavior and showed satisfactory results. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.007

文献信息

• Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(.omega.-phenyl-.omega.-hydroxyalkyl)imidazoles
  作者：Dante Nardi、Alberto Tajana、Amedeo Leonardi、Renzo Pennini、Ferruccio Portioli、Maria Jose Magistretti、Alessandro Subissi

  DOI：10.1021/jm00138a017

  日期：1981.6

  A novel series of N-(benzoylalkyl)imidazoles and N-(omega-phenyl-omega-hydroxyalkyl)imidazoles was synthesized and evaluated for anticonvulsant activity in mice against maximal electroshock induced seizures. Some of the compounds showed an activity comparable to or better than phenytoin and phenobarbital. The N-[beta-[4-(beta-phenylethyl)phenyl]-beta-hydroxyethyl]imidazole (38) was selected for further studies; preclinical toxicology and additional efficacy evaluations are in progress. Structure-activity relationships are discussed.
• NARDI, D.;TAJANA, A.;LEONARDI, A.;PENNINI, R.;PORTIOLI, F.;MAGISTRETTI, M+, J. MED. CHEM., 1981, 24, N 6, 727-731
  作者：NARDI, D.、TAJANA, A.、LEONARDI, A.、PENNINI, R.、PORTIOLI, F.、MAGISTRETTI, M+

  DOI：——

  日期：——
• Potholing of the hydrophobic heme oxygenase-1 western region for the search of potent and selective imidazole-based inhibitors
  作者：Loredana Salerno、Emanuele Amata、Giuseppe Romeo、Agostino Marrazzo、Orazio Prezzavento、Giuseppe Floresta、Valeria Sorrenti、Ignazio Barbagallo、Antonio Rescifina、Valeria Pittalà

  DOI：10.1016/j.ejmech.2018.02.007

  日期：2018.3

  Here we report the design, synthesis, and molecular modeling of new potent and selective imidazolebased HO-1 inhibitors in which the imidazole nucleus and the hydrophobic groups are linked by a phenylethanolic spacer. Most of the tested compounds showed a good inhibitor activity with IC50 values in the low micromolar range, with two of them (lb and 1j) exhibiting also high selectivity toward HO-2. These results were obtained by the idea of potholing the entire volume of the principal hydrophobic western region with an appropriate ligand volume. Molecular modeling studies showed that these molecules bind to the HO-1 in the consolidated fashion where the imidazolyl moiety coordinates the heme iron while the aromatic groups are stabilized by hydrophobic interaction in the western region of the binding pocket. Finally, the synthesized compounds were analyzed for in silico ADME-Tox properties to establish oral drug-like behavior and showed satisfactory results. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Tajana; Cappelletti; Leonardi, Arzneimittel Forschung, 1982, vol. 31, # 12, p. 2121 - 2123
  作者：Tajana、Cappelletti、Leonardi、Veronese

  DOI：——

  日期：——