5-(4-(2-(tetrahydropyran-2-yloxy)ethoxy)phenyl)-3H-1,2-dithiole-3-thione | 1314004-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-(2-(tetrahydropyran-2-yloxy)ethoxy)phenyl)-3H-1,2-dithiole-3-thione
• 英文别名: 5-[4-[2-(Oxan-2-yloxy)ethoxy]phenyl]dithiole-3-thione
• CAS: 1314004-82-4
• 化学式: C₁₆H₁₈O₃S₃
• 分子量: 354.515
• InChiKey: MWXVVPQTLWATLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-(2-(tetrahydropyran-2-yloxy)ethoxy)phenyl)-3H-1,2-dithiole-3-thione 在 N-甲基吗啉 、 甲醇 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 ((2-(4-(3-thioxo-3H-1,2-dithiol-5-yl)phenoxy)ethoxy)carbonyloxy)methyl 2-(acetyloxy)benzoate
  参考文献：
  名称：

  New Nitric Oxide or Hydrogen Sulfide Releasing Aspirins

  摘要：

  A new series of (((R-oxy)carbonyl)oxy)methyl esters of aspirin (ASA), bearing nitric oxide (NO) or hydrogen sulfide (H2S) releasing groups, was synthesized, and the compounds were evaluated as new ASA co-drugs. All the products were quite stable in buffered solution at pH 1 and 7.4. Conversely, they were all rapidly metabolized, producing ASA and the NO/H2S releasing moiety used for their preparation. Consequent on ASA release, the compounds were capable of inhibiting collagen-induced platelet aggregation of human platelet-rich plasma (PRP). The simple NO/H2S donor substructures were able to relax contracted rat aorta strips, with a NO- and H2S-dependent mechanism, respectively, but they either did not trigger antiaggregatory activity or displayed antiplatelet potency markedly below that of the related co-drug. The new products might provide a safer and improved alternative to the use of ASA principally in its anti-inflammatory and antithrombotic applications.

  DOI：

  10.1021/jm2004514
• 作为产物：
  描述：

  2-(四氢-2H-吡喃-2-氧基)乙醇 、 5-(4-羟基-苯基)-[1,2]二硫醇-3-硫酮 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到5-(4-(2-(tetrahydropyran-2-yloxy)ethoxy)phenyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  New Nitric Oxide or Hydrogen Sulfide Releasing Aspirins

  摘要：

  A new series of (((R-oxy)carbonyl)oxy)methyl esters of aspirin (ASA), bearing nitric oxide (NO) or hydrogen sulfide (H2S) releasing groups, was synthesized, and the compounds were evaluated as new ASA co-drugs. All the products were quite stable in buffered solution at pH 1 and 7.4. Conversely, they were all rapidly metabolized, producing ASA and the NO/H2S releasing moiety used for their preparation. Consequent on ASA release, the compounds were capable of inhibiting collagen-induced platelet aggregation of human platelet-rich plasma (PRP). The simple NO/H2S donor substructures were able to relax contracted rat aorta strips, with a NO- and H2S-dependent mechanism, respectively, but they either did not trigger antiaggregatory activity or displayed antiplatelet potency markedly below that of the related co-drug. The new products might provide a safer and improved alternative to the use of ASA principally in its anti-inflammatory and antithrombotic applications.

  DOI：

  10.1021/jm2004514