1-(biphenyl-4-yl)-2-(1H-imidazol-1-yl)ethanol | 73437-98-6

• 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: 1-(biphenyl-4-yl)-2-(1H-imidazol-1-yl)ethanol
• 英文别名: 1-Biphenyl-4-yl-2-imidazol-1-yl-ethanol；2-imidazol-1-yl-1-(4-phenylphenyl)ethanol
• CAS: 73437-98-6
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: YOHUWKWWIQCJSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  联苯-4-甲酰氯 、 1-(biphenyl-4-yl)-2-(1H-imidazol-1-yl)ethanol 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 1-(biphenyl-4-yl)-2-(1H-imidazol-1-yl)ethyl biphenyl-4-carboxylate
  参考文献：
  名称：

  2-（1 H-咪唑-1-基）-1-苯基乙醇衍生物作为抗原生动物的体外筛选及对克氏锥虫CYP51的对接研究

  摘要：

  甾醇14α-脱甲基酶（CYP51）是一种参与许多寄生虫原生动物（如锥虫和利什曼原虫）的存活和致病性的关键酶，因此代表了治疗运动质体疾病的重要药物靶标。从内部化合物库中选出的一组基于唑的化合物在体外针对不同的人类原生动物寄生虫进行了筛选。几种化合物显示出对克氏锥虫的选择性活性，其中化合物7的活性最高（IC 50 = 40 nM）。考虑到此处报道的化合物与已知的CYP51抑制剂之间的结构相似性，进行了分子对接研究，以评估其与原生动物靶标的结合并合理化生物学活性数据。

  DOI：

  10.1016/j.ejmech.2016.02.028
• 作为产物：
  描述：

  2'-氯代联苯乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 1-(biphenyl-4-yl)-2-(1H-imidazol-1-yl)ethanol
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(.omega.-phenyl-.omega.-hydroxyalkyl)imidazoles

  摘要：

  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.

  DOI：

  10.1021/jm00138a017

文献信息

• 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.
• Salerno; Sorrenti; Guerrera, Pharmazie, 1999, vol. 54, # 9, p. 685 - 690
  作者：Salerno、Sorrenti、Guerrera、Sarva、Siracusa、Di Giacomo、Vanella

  DOI：——

  日期：——
• Cozzi; Maggiori; Pillan, European Journal of Medicinal Chemistry, 1982, vol. 17, # 2, p. 139 - 143
  作者：Cozzi、Maggiori、Pillan、et al.

  DOI：——

  日期：——
• 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：——
• TAJANA, A.;CAPPELLETTI, R.;LEONARDI, A.;NARDI, D.;VERONESE, M., ARZNEIMITTEL-FORSCH., 1981, 31, N 12, 2121-2123
  作者：TAJANA, A.、CAPPELLETTI, R.、LEONARDI, A.、NARDI, D.、VERONESE, M.

  DOI：——

  日期：——