benzofuran-2-yl-(4-ethyl-phenyl)-methanone | 887908-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzofuran-2-yl-(4-ethyl-phenyl)-methanone
• 英文别名: 1-Benzofuran-2-yl-(4-ethylphenyl)methanone
• CAS: 887908-66-9
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: ZHCDODFFNOCVPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzofuran-2-yl-(4-ethyl-phenyl)-methanone 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 99.0h， 生成 1-[Benzofuran-2-yl-(4-ethyl-phenyl)-methyl]-1H-[1,2,4]triazole
  参考文献：
  名称：

  Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles

  摘要：

  Methodology previously described by our group was applied to the preparation of a series of 4-alkyl/aryl-substituted 1-[benzofuran-2-yl-phenylmethyl]-1H-triazoles. The [1,2,4]-triazole derivatives were prepared for a range of alkyl and aryl substituents, and for the 4-methyl, 4-ethyl, 4-'propyl, 4-'butyl, 4-phenyl and 4-chlorophenyl derivatives, the minor [1,3,4]-triazole isomer also isolated. All the triazole derivatives were evaluated for CYP26A1 inhibitory activity using a MCF-7 cell-based assay. The 4-ethyl and 4-phenyl-1,2,4-triazole derivatives displayed inhibitory activity (IC50 4.5 and 7 mu M, respectively) comparable with that of the CYP26 inhibitor liarozole (IC50 7 mu M). Using a CYP26A1 homology model (based on CYP3A4) template, docking experiments were performed with MOE with multiple hydrophobic interactions observed in addition to coordination between the triazole nitrogen and the haem transition metal. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.018
• 作为产物：
  描述：

  邻甲基苄醇 、 2-溴-1-(4-乙基苯基)乙酮 在 sodium hydride 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以34%的产率得到benzofuran-2-yl-(4-ethyl-phenyl)-methanone
  参考文献：
  名称：

  Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles

  摘要：

  Methodology previously described by our group was applied to the preparation of a series of 4-alkyl/aryl-substituted 1-[benzofuran-2-yl-phenylmethyl]-1H-triazoles. The [1,2,4]-triazole derivatives were prepared for a range of alkyl and aryl substituents, and for the 4-methyl, 4-ethyl, 4-'propyl, 4-'butyl, 4-phenyl and 4-chlorophenyl derivatives, the minor [1,3,4]-triazole isomer also isolated. All the triazole derivatives were evaluated for CYP26A1 inhibitory activity using a MCF-7 cell-based assay. The 4-ethyl and 4-phenyl-1,2,4-triazole derivatives displayed inhibitory activity (IC50 4.5 and 7 mu M, respectively) comparable with that of the CYP26 inhibitor liarozole (IC50 7 mu M). Using a CYP26A1 homology model (based on CYP3A4) template, docking experiments were performed with MOE with multiple hydrophobic interactions observed in addition to coordination between the triazole nitrogen and the haem transition metal. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.018

文献信息

• Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles
  作者：Stephane Pautus、Sook Wah Yee、Martyn Jayne、Michael P. Coogan、Claire Simons

  DOI：10.1016/j.bmc.2006.01.018

  日期：2006.6

  Methodology previously described by our group was applied to the preparation of a series of 4-alkyl/aryl-substituted 1-[benzofuran-2-yl-phenylmethyl]-1H-triazoles. The [1,2,4]-triazole derivatives were prepared for a range of alkyl and aryl substituents, and for the 4-methyl, 4-ethyl, 4-'propyl, 4-'butyl, 4-phenyl and 4-chlorophenyl derivatives, the minor [1,3,4]-triazole isomer also isolated. All the triazole derivatives were evaluated for CYP26A1 inhibitory activity using a MCF-7 cell-based assay. The 4-ethyl and 4-phenyl-1,2,4-triazole derivatives displayed inhibitory activity (IC50 4.5 and 7 mu M, respectively) comparable with that of the CYP26 inhibitor liarozole (IC50 7 mu M). Using a CYP26A1 homology model (based on CYP3A4) template, docking experiments were performed with MOE with multiple hydrophobic interactions observed in addition to coordination between the triazole nitrogen and the haem transition metal. (c) 2006 Elsevier Ltd. All rights reserved.