N-(3,4-dihydro-2-hexyl-6-methoxy-2,7,8-trimethyl-2H-benzopyran-5-carbonyl)-N',N'-ethylenediamine | 389634-05-3

• 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: N-(3,4-dihydro-2-hexyl-6-methoxy-2,7,8-trimethyl-2H-benzopyran-5-carbonyl)-N',N'-ethylenediamine
• 英文别名: N-(3,4-dihydro-2-hexyl-6-methoxy 2,7,8-trimethyl-2H-1-benzopyran-5-carbonyl)-N',N'-diethyl ethylenediamine；N-[2-(diethylamino)ethyl]-2-hexyl-6-methoxy-2,7,8-trimethyl-3,4-dihydrochromene-5-carboxamide
• CAS: 389634-05-3
• 化学式: C₂₆H₄₄N₂O₃
• 分子量: 432.647
• InChiKey: VCWOMQMAQPLNGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3,4-dihydro-2-hexyl-6-methoxy-2,7,8-trimethyl-2H-benzopyran-5-carbonyl)-N',N'-ethylenediamine 在 sodium hydride 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到N-(3,4-dihydro-6-hydroxy-2-hexyl-2,7,8-trimethyl-2H-1-benzopyran-5-carbonyl)-N',N'-diethyl ethylenediamine
  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：

  3-甲基-1-壬烯-3-醇 在 sodium chlorite 、 sodium dihydrogenphosphate 、 氯化亚砜 、 双氧水 、 四氯化钛 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 15.0h， 生成 N-(3,4-dihydro-2-hexyl-6-methoxy-2,7,8-trimethyl-2H-benzopyran-5-carbonyl)-N',N'-ethylenediamine
  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 POSSESSING ANTIOXIDANT AND ANTIARRHYTHMIC ACTIVITY
  申请人：Uni-Pharma Kleon Tsetis Pharmaceutical Laboratories S.A.

  公开号：EP1301504B1

  公开（公告）日：2004-11-03
• Bifunctional agents possessing antioxidant and antiarrhythmic activity
  申请人：——

  公开号：US20040259763A1

  公开（公告）日：2004-12-23

  The present invention relates to novel bifunctional agents possessing antioxidant and antiarrhytmic activity, methods for the synthesis of the same and their applications in treating ischemia-reperfusion injury, as well as a variety of disorders related to free radicals and/or arrhythmias. These bifunctional drugs should prefrentially segregate in the membrane and produce their antiarrhytmic effects while, at the same time, help in protecting the membrane lipids by scavenging free radicals. The present invention comprises compounds represented by Formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 are further defined. 1
• US7115657B2
  申请人：——

  公开号：US7115657B2

  公开（公告）日：2006-10-03
• 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.