3,4-dihydro-2-hexyl-6-hydroxy-5,7,8-trimethyl-2H-1-benzopyran-2-carboxylic acid | 389633-93-6

• 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: 3,4-dihydro-2-hexyl-6-hydroxy-5,7,8-trimethyl-2H-1-benzopyran-2-carboxylic acid
• 英文别名: 2-Hexyl-6-hydroxy-5,7,8-trimethyl-3,4-dihydrochromene-2-carboxylic acid
• CAS: 389633-93-6
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: RLFAFQYXGHWHQO-UHFFFAOYSA-N

物化性质

• 沸点：
  499.3±45.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二乙基乙二胺 、 3,4-dihydro-2-hexyl-6-hydroxy-5,7,8-trimethyl-2H-1-benzopyran-2-carboxylic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以65.5%的产率得到N-(3,4-dihydro-6-hydroxy-2-hexyl-5,7,8-trimethyl-2H-1-benzopyran-2-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：

  3,4-dihydro-2-hexyl-6-hydroxy-5,7,8-trimethyl-2H-1-benzopyran-2-carbonitrile 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 以79.1%的产率得到3,4-dihydro-2-hexyl-6-hydroxy-5,7,8-trimethyl-2H-1-benzopyran-2-carboxylic acid
  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
• COMPOSITIONS AND METHODS FOR THE PREVENTION AND/OR TREATMENT OF MITOCHONDRIAL DISEASE, INCLUDING FRIEDREICH'S ATAXIA
  申请人：Keefe Dennis

  公开号：US20210206736A1

  公开（公告）日：2021-07-08

  The disclosure provides therapeutic compositions (i.e., therapeutic agents) and methods of preventing or treating Friedreich's ataxia in a mammalian subject, reducing risk factors, signs and/or symptoms associated with Friedreich's ataxia (e.g., Complex I deficiency), and/or reducing the likelihood or severity of Friedreich's ataxia. The disclosure further provides novel intermediates for the production of said therapeutic compositions and related reduced versions of said therapeutic compositions, which reduce forms may also be used as therapeutic agents (or prodrugs of the therapeutic agent(s)).
• US7115657B2
  申请人：——

  公开号：US7115657B2

  公开（公告）日：2006-10-03
• [EN] BIFUNCTIONAL AGENTS POSSESSING ANTIOXIDANT AND ANTIARRHYTHMIC ACTIVITY<br/>[FR] AGENTS BIFONCTIONNELS A ACTIVITE ANTIOXYDANTE ET ANTIARYTHMIQUE
  申请人：UNI PHARMA KLEON TSETIS PHARMACEUTICAL LAB SA

  公开号：WO2002004438A1

  公开（公告）日：2002-01-17

  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 preferentially 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 R1, R2, R3, R4, R5 are further defined.