1-(4-苯氧基苯基)-1-羟基-2-(咪唑-1-基)-乙烷 | 66250-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-苯氧基苯基)-1-羟基-2-(咪唑-1-基)-乙烷
• 英文名称: 2-(1H-imidazol-1-yl)-1-(4-phenoxyphenyl)ethanol
• 英文别名: 1-(4-phenoxyphenyl)-1-hydroxy-2-(imidazol-1-yl)-ethane；2-Imidazol-1-yl-1-(4-phenoxyphenyl)ethanol
• CAS: 66250-36-0
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: JGJOCYKOFLNFKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-苯氧基苯基)-1-羟基-2-(咪唑-1-基)-乙烷 、 氯化苄 以45%的产率得到
  参考文献：
  名称：

  TAJANA, A.;CAPPELLETTI, R.;LEONARDI, A.;NARDI, D.;VERONESE, M., ARZNEIMITTEL-FORSCH., 1981, 31, N 12, 2121-2123

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-1-(4-苯氧基苯基)乙酮 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 1-(4-苯氧基苯基)-1-羟基-2-(咪唑-1-基)-乙烷
  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

• Pesticidally active 1-acyloxy-1-phenyl-2-azolyl-ethanes
  申请人：Bayer Aktiengesellschaft

  公开号：US04349556A1

  公开（公告）日：1982-09-14

  1-Acyloxy-1-phenyl-2-azolyl-ethanes of the formula ##STR1## in which R represents halogen, alkyl, alkoxy, alkylthio, alkylsulphonyl, haloalkyl, nitro, cyano, optionally substituted phenyl or optionally substituted phenoxy, R' represents alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl, optionally substituted phenoxyalkyl, amino, alkylamino, dialkylamino, alkyl-alkyl-carbonylamino or optionally substituted phenylamino, A represents a CH-group or a nitrogen atom, and n represents 0, 1, 2, 3, 4 or 5, or salts thereof, which possess fungicidal, bactericidal and nematicidal properties.

  公式为##STR1##的1-酰氧基-1-苯基-2-咪唑基乙烷，其中R代表卤素、烷基、烷氧基、烷硫基、烷基磺酰基、卤代烷基、硝基、氰基、可选择取代的苯基或可选择取代的苯氧基，R'代表烷基、烯基、炔基、环烷基、卤代烷基、可选择取代的苯基、可选择取代的苯基烷基、可选择取代的苯氧基烷基、氨基、烷基氨基、二烷基氨基、烷基-烷基-羰基氨基或可选择取代的苯基氨基，A代表一个CH基团或一个氮原子，n代表0、1、2、3、4或5，或其盐，具有杀菌、杀菌和杀线虫作用。
• 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：——
• US4349556A
  申请人：——

  公开号：US4349556A

  公开（公告）日：1982-09-14
• Tajana; Cappelletti; Leonardi, Arzneimittel Forschung, 1982, vol. 31, # 12, p. 2121 - 2123
  作者：Tajana、Cappelletti、Leonardi、Veronese

  DOI：——

  日期：——