ethyl 2-(2-bromobenzyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalene carboxylate | 1253049-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2-(2-bromobenzyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalene carboxylate
• 英文别名: Ethyl 2-[(2-bromophenyl)methyl]-6-methoxy-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• CAS: 1253049-91-0
• 化学式: C₂₁H₂₁BrO₄
• 分子量: 417.299
• InChiKey: XVJXOYWPPASRFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-bromobenzyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalene carboxylate 在 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.5h， 以26%的产率得到2-(2-bromobenzyl)-6-methoxy-tetralone
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones

  摘要：

  A series of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones were prepared, using an efficient synthetic scheme, and evaluated for their inhibitory activity against cytochrome P450C24A1 (CYP24A1) hydroxylase. In general the reduced benzyl tetralones were more active than the parent benzylidene tetralones. The 2-ethyl and 2-trifluoromethyl benzyl tetralone derivatives (4c and 4b) showed optimal activity in this series with IC(50) values of 1 92 mu M and 2.08 mu M, respectively compared with the standard ketoconazole IC(50) 0.52 mu M. The 2-bromobenzyl tetralone (4d) showed a preference for CYP27A1 (IC(50) 59 nM) over CYP24A1 (IC(50) 163 mu M) and may be a useful lead in CYP27A1 inhibition studies The 2-ethylphenyl benzyl derivative (9c), which showed weak activity against the wild type CYP24A1 (IC(50) 25.57 mu M), exhibited enhanced inhibitory activity towards L148F and M416T mutants, this difference in activity for the L148F mutant has been explained using molecular modelling (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.001
• 作为产物：
  描述：

  ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 、 2-溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.0h， 以69%的产率得到ethyl 2-(2-bromobenzyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalene carboxylate
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones

  摘要：

  A series of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones were prepared, using an efficient synthetic scheme, and evaluated for their inhibitory activity against cytochrome P450C24A1 (CYP24A1) hydroxylase. In general the reduced benzyl tetralones were more active than the parent benzylidene tetralones. The 2-ethyl and 2-trifluoromethyl benzyl tetralone derivatives (4c and 4b) showed optimal activity in this series with IC(50) values of 1 92 mu M and 2.08 mu M, respectively compared with the standard ketoconazole IC(50) 0.52 mu M. The 2-bromobenzyl tetralone (4d) showed a preference for CYP27A1 (IC(50) 59 nM) over CYP24A1 (IC(50) 163 mu M) and may be a useful lead in CYP27A1 inhibition studies The 2-ethylphenyl benzyl derivative (9c), which showed weak activity against the wild type CYP24A1 (IC(50) 25.57 mu M), exhibited enhanced inhibitory activity towards L148F and M416T mutants, this difference in activity for the L148F mutant has been explained using molecular modelling (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.001

文献信息

• Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones
  作者：Ahmed S. Aboraia、Bart Makowski、Alba Bahja、David Prosser、Andrea Brancale、Glenville Jones、Claire Simons

  DOI：10.1016/j.ejmech.2010.07.001

  日期：2010.10

  A series of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones were prepared, using an efficient synthetic scheme, and evaluated for their inhibitory activity against cytochrome P450C24A1 (CYP24A1) hydroxylase. In general the reduced benzyl tetralones were more active than the parent benzylidene tetralones. The 2-ethyl and 2-trifluoromethyl benzyl tetralone derivatives (4c and 4b) showed optimal activity in this series with IC(50) values of 1 92 mu M and 2.08 mu M, respectively compared with the standard ketoconazole IC(50) 0.52 mu M. The 2-bromobenzyl tetralone (4d) showed a preference for CYP27A1 (IC(50) 59 nM) over CYP24A1 (IC(50) 163 mu M) and may be a useful lead in CYP27A1 inhibition studies The 2-ethylphenyl benzyl derivative (9c), which showed weak activity against the wild type CYP24A1 (IC(50) 25.57 mu M), exhibited enhanced inhibitory activity towards L148F and M416T mutants, this difference in activity for the L148F mutant has been explained using molecular modelling (C) 2010 Elsevier Masson SAS. All rights reserved.