3,4-dihydro-2-(2-methylthioethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol | 169824-13-9

• 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-(2-methylthioethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol
• 英文别名: 2,5,7,8-tetramethyl-2-(2-methylsulfanylethyl)-3,4-dihydrochromen-6-ol
• CAS: 169824-13-9
• 化学式: C₁₆H₂₄O₂S
• 分子量: 280.431
• InChiKey: YIVXWBDLMPGLPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸甲酯 、 3,4-dihydro-2-(2-methylthioethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol 以 乙腈 为溶剂， 反应 24.0h， 以87%的产率得到[2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethyl]dimethylsulfonium, 4-methylbenzenesulfonate
  参考文献：
  名称：

  Cardioselective Ammonium, Phosphonium, and Sulfonium Analogs of .alpha.-Tocopherol and Ascorbic Acid That Inhibit in Vitro and ex Vivo Lipid Peroxidation and Scavenge Superoxide Radicals

  摘要：

  Analogues of alpha-tocopherol and ascorbic acid with permanently cationic substituents, i.e., phosphonium (8, 9), sulfonium (11), acylhydrazinium (13, 14), and ammonium (1, 16, 21), were synthesized, and the 2R and 2S enantiomers of the alpha-tocopherol analogues 1, 8, 11, and 13 were separated. The compounds were found to scavenge lipoperoxyl and superoxide radicals in vitro and accumulate in heart tissue (cardioselectivity) as demonstrated by measurement of ex vivo inhibition of lipid peroxidation in mouse heart homogenates and confirmed by HPLC determination of drug concentrations for 1 and 11. The 2R and 2S enantiomers of 1 inhibited ex vivo lipid peroxidation to an equal extent. Thus the in vivo uptake into myocytes (cardioselectivity) is independent of the geometry at the chiral center and common to permanently cationic compounds.

  DOI：

  10.1021/jm00015a010
• 作为产物：
  描述：

  2-(2-bromoethyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol 、 sodium thiomethoxide 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以70%的产率得到3,4-dihydro-2-(2-methylthioethyl)-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol
  参考文献：
  名称：

  Cardioselective Ammonium, Phosphonium, and Sulfonium Analogs of .alpha.-Tocopherol and Ascorbic Acid That Inhibit in Vitro and ex Vivo Lipid Peroxidation and Scavenge Superoxide Radicals

  摘要：

  Analogues of alpha-tocopherol and ascorbic acid with permanently cationic substituents, i.e., phosphonium (8, 9), sulfonium (11), acylhydrazinium (13, 14), and ammonium (1, 16, 21), were synthesized, and the 2R and 2S enantiomers of the alpha-tocopherol analogues 1, 8, 11, and 13 were separated. The compounds were found to scavenge lipoperoxyl and superoxide radicals in vitro and accumulate in heart tissue (cardioselectivity) as demonstrated by measurement of ex vivo inhibition of lipid peroxidation in mouse heart homogenates and confirmed by HPLC determination of drug concentrations for 1 and 11. The 2R and 2S enantiomers of 1 inhibited ex vivo lipid peroxidation to an equal extent. Thus the in vivo uptake into myocytes (cardioselectivity) is independent of the geometry at the chiral center and common to permanently cationic compounds.

  DOI：

  10.1021/jm00015a010

文献信息

• Tissue protective tocopherol analogs
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05484810A1

  公开（公告）日：1996-01-16

  This invention relates to alkylated sulfonium alkylene derivatives of certain 2H-1-benzopyrans, to the intermediates and processes useful for their preparation, to their free-radical scavenger and cardioprotective properties and to their end-use application as therapeutic agents.

  本发明涉及某些2H-1-苯并吡喃的烷基磺鎓烷基衍生物，以及用于其制备的中间体和过程，其自由基清除剂和心脏保护性能，以及它们作为治疗剂的最终应用。
• US5484810A
  申请人：——

  公开号：US5484810A

  公开（公告）日：1996-01-16
• Cardioselective Ammonium, Phosphonium, and Sulfonium Analogs of .alpha.-Tocopherol and Ascorbic Acid That Inhibit in Vitro and ex Vivo Lipid Peroxidation and Scavenge Superoxide Radicals
  作者：J. Martin Grisar、Gilbert Marciniak、Frank N. Bolkenius、Joelle Verne-Mismer、Eugene R. Wagner

  DOI：10.1021/jm00015a010

  日期：1995.7

  Analogues of alpha-tocopherol and ascorbic acid with permanently cationic substituents, i.e., phosphonium (8, 9), sulfonium (11), acylhydrazinium (13, 14), and ammonium (1, 16, 21), were synthesized, and the 2R and 2S enantiomers of the alpha-tocopherol analogues 1, 8, 11, and 13 were separated. The compounds were found to scavenge lipoperoxyl and superoxide radicals in vitro and accumulate in heart tissue (cardioselectivity) as demonstrated by measurement of ex vivo inhibition of lipid peroxidation in mouse heart homogenates and confirmed by HPLC determination of drug concentrations for 1 and 11. The 2R and 2S enantiomers of 1 inhibited ex vivo lipid peroxidation to an equal extent. Thus the in vivo uptake into myocytes (cardioselectivity) is independent of the geometry at the chiral center and common to permanently cationic compounds.