5-amino-3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran | 389634-12-2

• 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: 5-amino-3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran
• 英文别名: 6-methoxy-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-5-ylamine；6-Methoxy-2,2,7,8-tetramethyl-3,4-dihydrochromen-5-amine
• CAS: 389634-12-2
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: AMEAPRNQKKQLOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran 在 sodium hydride 、 三乙胺 、 乙硫醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.0h， 生成 N-(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)-(diethylamino)-acetamide
  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：

  2,2,7,8-四甲基-6-色满醇 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-3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-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

文献信息

• Chroman/Catechol Hybrids:  Synthesis and Evaluation of Their Activity against Oxidative Stress Induced Cellular Damage
  作者：Maria Koufaki、Elissavet Theodorou、Dimitrios Galaris、Lambros Nousis、Efrosini S. Katsanou、Michael N. Alexis

  DOI：10.1021/jm0506120

  日期：2006.1.1

  chromans substituted at positions 2 or 5 by catechol derivatives were synthesized, and their activity against oxidative stress induced cellular damage was studied. Specifically, the ability of the new molecules to protect cultured cells from H(2)O(2)-induced DNA damage was evaluated using single cell gel electrophoresis (comet assay), while the neuroprotective activity of the new compounds against oxidative

  合成了三类在邻苯二酚衍生物在2或5位取代的苯并二氢吡喃，并研究了它们对氧化应激诱导的细胞损伤的活性。具体来说，使用单细胞凝胶电泳（彗星试验）评估了新分子保护培养的细胞免受H（2）O（2）诱导的DNA损伤的能力，而新化合物针对氧化应激诱导的神经保护活性被编程使用谷氨酸-challanged海马HT22细胞研究了细胞死亡。大多数新化合物比槲皮素具有更强的神经保护作用。5-取代的苯并二氢吡喃类似物，例如咖啡酰胺12和16和二氢二苯乙烯类似物24，分别对Jurkat T细胞和HT22细胞中H（2）O（2）-和谷氨酸诱导的损伤最有效。
• Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias
  作者：Maria Koufaki、Anastasia Detsi、Elissavet Theodorou、Christina Kiziridi、Theodora Calogeropoulou、Athanasios Vassilopoulos、Angeliki P. Kourounakis、Eleni Rekka、Panos N. Kourounakis、Catherine Gaitanaki、Panagiota Papazafiri

  DOI：10.1016/j.bmc.2004.07.012

  日期：2004.9

  Novel hybrids of lipoic acid and trolox connected through triamine spacers as well as analogues in which the lipoic acid was attached at different positions of the chroman moiety of vitamin E through an amide bond, were synthesized and exhibited strong inhibition of the microsomal lipid peroxidation. Moreover, the new molecules, at 1 muM concentration, reduced reperfusion arrhythimas and MDA content on isolated rat heart preparations, with the 2- and 5-subtituted chromans possessing the better cardioprotective activity. (C) 2004 Elsevier Ltd. All rights reserved.
• 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