2-hexyl-6-hydroxy-2,7,8-trimethylchroman | 654673-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-hexyl-6-hydroxy-2,7,8-trimethylchroman
• 英文别名: 2-Hexyl-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-6-ol；2-hexyl-2,7,8-trimethyl-3,4-dihydrochromen-6-ol
• CAS: 654673-45-7
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: YWHWZLNPWBODGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hexyl-6-hydroxy-2,7,8-trimethylchroman 在 sodium tetrahydroborate 、 硝酸乙酸酐 、 乙酸酐 、 potassium carbonate 、 溶剂黄146 、 copper(l) chloride 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 10.0h， 生成 5-amino-2-hexyl-3,4-dihydro-6-methoxy-2,7,8-trimethyl-2H-1-benzopyran
  参考文献：
  名称：

  Bifunctional agents for reperfusion arrhythmias: Novel hybrid vitamin E/Class I antiarrhythmics

  摘要：

  We have synthesized a series of hybrid compounds combining the pharmacophoric redox moieties of vitamin E and key features responsible for the antiarrhythmic properties of the class I antiarrhythmics procainamide and lidocaine. Procainamide analogue (2a) and lidocaine analogues (14a) and (14b) are very strong inhibitors of lipid peroxidation. All analogues tested at 100 or 30 muM enhanced the post ischemic recovery without inducing ventricular fibrillations while there was no evidence in our experiments for drug-induced pro-arrhythmia. In addition, they induced a widening of the QRS intervals. Our data suggest that the efficacy of the new compounds in preventing reperfusion arrhythmias could be attributed to their combined effects involving inhibition of free radical mediated damage coupled with antiarrhythmic properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.010
• 作为产物：
  描述：

  溴己烷 在 lithium 、 溶剂黄146 作用下， 以 乙醚 、 异丙醚 为溶剂， 反应 5.0h， 生成 2-hexyl-6-hydroxy-2,7,8-trimethylchroman
  参考文献：
  名称：

  Bifunctional agents for reperfusion arrhythmias: Novel hybrid vitamin E/Class I antiarrhythmics

  摘要：

  We have synthesized a series of hybrid compounds combining the pharmacophoric redox moieties of vitamin E and key features responsible for the antiarrhythmic properties of the class I antiarrhythmics procainamide and lidocaine. Procainamide analogue (2a) and lidocaine analogues (14a) and (14b) are very strong inhibitors of lipid peroxidation. All analogues tested at 100 or 30 muM enhanced the post ischemic recovery without inducing ventricular fibrillations while there was no evidence in our experiments for drug-induced pro-arrhythmia. In addition, they induced a widening of the QRS intervals. Our data suggest that the efficacy of the new compounds in preventing reperfusion arrhythmias could be attributed to their combined effects involving inhibition of free radical mediated damage coupled with antiarrhythmic properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.010

文献信息

• Bifunctional agents for reperfusion arrhythmias: Novel hybrid vitamin E/Class I antiarrhythmics
  作者：Maria Koufaki、Theodora Calogeropoulou、Eleni Rekka、Michael Chryselis、Panagiota Papazafiri、Catherine Gaitanaki、Alexandros Makriyannis

  DOI：10.1016/j.bmc.2003.08.010

  日期：2003.11

  We have synthesized a series of hybrid compounds combining the pharmacophoric redox moieties of vitamin E and key features responsible for the antiarrhythmic properties of the class I antiarrhythmics procainamide and lidocaine. Procainamide analogue (2a) and lidocaine analogues (14a) and (14b) are very strong inhibitors of lipid peroxidation. All analogues tested at 100 or 30 muM enhanced the post ischemic recovery without inducing ventricular fibrillations while there was no evidence in our experiments for drug-induced pro-arrhythmia. In addition, they induced a widening of the QRS intervals. Our data suggest that the efficacy of the new compounds in preventing reperfusion arrhythmias could be attributed to their combined effects involving inhibition of free radical mediated damage coupled with antiarrhythmic properties. (C) 2003 Elsevier Ltd. All rights reserved.