(R)-(+)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid | 53730-40-8

• 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: (R)-(+)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid
• 英文别名: (2R)-(+)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid；(R)-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)acetic acid；R-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid；2-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl]acetic acid
• CAS: 53730-40-8
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: IETSMPQISKAPQX-OAHLLOKOSA-N

物化性质

• 沸点：
  465.8±45.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (R)-(+)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82.5%的产率得到(R)-2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethanol
  参考文献：
  名称：

  非甾体抗炎羧酸的新型酯和酰胺，可作为抗氧化剂和抗增殖剂。

  摘要：

  非甾体抗炎药萘普生的一系列酚类抗氧化剂酯和酰胺衍生物被设计为具有抗炎和细胞保护活性。在膜脂质过氧化测定中通过硫代巴比妥酸反应性物质（TBARS）的形成间接评估了化合物的抗氧化活性，并通过抑制了人类血管内皮细胞中DNA的合成来确定其抗增殖活性。该系列化合物表现出有效的抗氧化活性，IC50值（1.6-11.63 microM）比Trolox（6-羟基-2,5,7,8-四甲基苯并二甲酸）和400的IC50值低2-6倍。比维生素E低-1300倍。酯或酰胺亚结构的结构修饰（5a和6a）不影响抗氧化活性，但是6-羟基取代基的甲基化产生了没有抗氧化活性的化合物6f。尽管抗氧化剂活性没有区别，但是酰胺衍生物作为抗增殖剂往往比相应的酯更有效。酰胺衍生物（3、5a-e，8）的IC50范围为2至7 microM，而与结构相关的酯（1、2a-c，6a-e）的IC50范围为9至22 microM。此外，对化合物6a

  DOI：

  10.1021/jm980430o
• 作为产物：
  描述：

  3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2,6-diol 在 氢氧化钾 、 水 作用下， 以 乙二醇 为溶剂， 反应 21.5h， 生成 (R)-(+)-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetic acid
  参考文献：
  名称：

  Cohen, Noal; Banner, Bruce L.; Neukom, Christian, Synthetic Communications, 1982, vol. 12, # 1, p. 57 - 66

  摘要：

  DOI：

文献信息

• Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
  申请人：——

  公开号：US20030236227A1

  公开（公告）日：2003-12-25

  The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

  该发明提供了在治疗2型糖尿病中有用的药物化合物。这些化合物具有优势，因为它们可以被代谢药物解毒系统迅速代谢。特别地，设计了包含酯基的噻唑烷二酮类似物的化合物。该发明还涉及治疗疾病的方法，如糖尿病，包括给予经设计为能够被血清或细胞内酯酶代谢的化合物的治疗有效组合物。还教授了含酯基的噻唑烷二酮类似物的药物组合物。
• 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.

  本发明涉及某些2H-1-苯并吡喃衍生物的季铵盐，其中间体和有用于其制备的过程，以及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。
• 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.
• THIAZOLIDINEDIONE ANALOGUES AND THEIR USE FOR THE TREATMENT OF DIABETES
  申请人：ARYx Therapeutics

  公开号：EP1276730A2

  公开（公告）日：2003-01-22
• ARYL DERIVATIVES FOR THE TREATMENT OF DIABETES, HYPERLIPIDEMIA, HYPERCHOLESTEROLEMIA AND ATHEROSCLEROSIS
  申请人：Aryx Therapeutics

  公开号：EP1430039A2

  公开（公告）日：2004-06-23