3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ethanol | 79907-48-5

• 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-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ethanol
• 英文别名: 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethanol；2-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)ethanol；2-(2-hydroxyethyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol
• CAS: 79907-48-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: RUYZTDOMKYWHFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ethanol 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 3,4-dihydro-6-hydroxy-N,N,N,2,5,7,8-heptamethyl-2H-1-benzopyran-2-ethanaminium 4-methylbenzenesulfonate
  参考文献：
  名称：

  A cardioselective, hydrophilic N,N,N-trimethylethanaminium .alpha.-tocopherol analog that reduces myocardial infarct size

  摘要：

  The alpha-tocopherol analogue 3,4-dihydro-6-hydroxy-N,N,N,2,5,7,8-heptamethyl-2H-1-benzopyran-2-ethanaminium 4-methylbenzenesulfonate (1a, MDL 73404) and its O-acetate 1b (MDL 74270) were synthesized. Compound 1a was found to be hydrophilic (log P = -0.60) and to prevent lipid autoxidation in rat brain homogenate with an IC50 of 1.7 +/- 0.9-mu-M. Tissue distribution studies with [C-14]-1b in rats (1 mg/kg iv) showed that radioactivity accumulates in the heart (ratio 20:1 vs blood after 1 h). Infusion of 1 mg/kg per h of 1b bromide reduced infarct size by 54% in rats subjected to coronary artery occlusion for 60 min followed by reperfusion for 30 min, compared to saline-infused controls. By comparison, the tertiary amine analogue 5 was found not to accumulate in heart tissue, to be an equally effective free-radical scavenger in vitro, but to require a higher dose to reduce infarct size in rats. This shows that the cardioselectivity of compound 1 contributes to its potency in salvaging myocardial tissue in rats after ischemia and reperfusion.

  DOI：

  10.1021/jm00105a040
• 作为产物：
  描述：

  methyl 2-(6-acetoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)acetate 在 sodium sulfate 作用下， 生成 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ethanol
  参考文献：
  名称：

  Benzopyran derivatives

  摘要：

  苯并吡喃衍生物的化学式为：##STR1## 其中变量在规范中有定义，以及其药用酸盐具有对美拉德反应的抑制活性和抗氧化作用，因此对于预防和治疗多种糖尿病并发症、老化引起的疾病以及因过氧化脂肪形成引起的多种疾病是有用的。

  公开号：

  US05055598A1

文献信息

• Cardioprotective tocopherol analogs
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05500444A1

  公开（公告）日：1996-03-19

  This invention relates to quaternary ammonium salts of certain 2H-1-benzopyran derivatives, to the intermediates and processes useful for their preparation, to their free-radical scavenger and cellular protective properties and to their end-use application as therapeutic agents.

  这项发明涉及某些2H-1-苯并吡喃衍生物的季铵盐，以及用于它们的制备的中间体和过程，它们的自由基清除剂和细胞保护性能，以及它们作为治疗剂的最终应用。
• Cholesterol-lowering tocopherol analogs
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05135945A1

  公开（公告）日：1992-08-04

  This invention relates to alkylamino alkylene derivatives of certain 2H-1-benzopyrans useful as plasma cholesterol lowering agents and to their end-use application as therapeutic agents.

  这项发明涉及某些2H-1-苯并吡喁酮的烷基氨基烷基衍生物，可用作降低血浆胆固醇的药物，并涉及它们作为治疗剂的最终应用。
• [EN] COMPOSITIONS CAPABLE OF INHIBITING REACTIVE OXYGEN AND CARBONYL SPECIES<br/>[FR] COMPOSITIONS CAPABLES D'INHIBER LES ESPECES A OXYGENE ET CARBONYLE REACTIFS
  申请人：BAXTER INT

  公开号：WO2006019855A1

  公开（公告）日：2006-02-23

  Therapeutic compositions are provided. The compositions include a single molecule that can display both antioxidant and carbonyl trapping properties. This can effectively reduce inflammation, oxidative stress and carbonyl stress, such as to prevent and/or treat cardiovascular disease and inflammatory diseases in kidney disease patients.

  提供了治疗性组合物。这些组合物包括一种单一分子，它既具有抗氧化性又具有羰基捕获性能。这可以有效减少炎症、氧化应激和羰基应激，从而预防和/或治疗肾脏疾病患者的心血管疾病和炎症性疾病。
• FRIEDEL–CRAFTS REACTION OF 3,6-DIHYDRO-4-METHYL-2<i>H</i>-PYRAN WITH PHENOLS. A CONVENIENT SYNTHESIS OF A KEY INTERMEDIATE OF ALPHA-TOCOPHEROL
  作者：Yoshiji Fujita、Manzo Shiono、Katsushi Ejiri、Kazumi Saita

  DOI：10.1246/cl.1985.1399

  日期：1985.9.5

  The Friedel–Crafts reaction of 3,6-dihydro-4-methyl-2H-pyran with 2,3,5-trimethylhydroquinone afforded 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ethanol in good yield.

  3,6-二氢-4-甲基-2H-吡喃与2,3,5-三甲基氢醌的Friedel-Crafts反应得到3,4-二氢-6-羟基-2,5,7,8-四甲基-2H- 1-苯并吡喃-2-乙醇收率良好。
• 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.

  本发明涉及特定的2H-1-苯并吡喃类化合物的烷基磺鎓烷基衍生物，以及其制备过程中有用的中间体和方法，以及它们的自由基清除剂和心脏保护性质，以及它们作为治疗剂的最终应用。

表征谱图