10-Methoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene | 677032-53-0

• 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: 10-Methoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene
• 英文别名: 5-Methoxy-2-(methylsulfanyl)-5H-[1]benzopyrano[4,3-d]pyrimidine；5-methoxy-2-methylsulfanyl-5H-chromeno[4,3-d]pyrimidine
• CAS: 677032-53-0
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: OWNLDKPYFBQRTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-Methoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以83%的产率得到3-Methanesulfonyl-10-methoxy-10H-9-oxa-2,4-diaza-phenanthrene
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 5H-[1]benzopyrano[4,3-d]pyrimidines effective as antiplatelet/analgesic agents

  摘要：

  Synthesis and pharmacological screening of new2-methylthio/2-methanesulfonyl/2-methoxy-5H-[1]benzopyrano[4,3-d]pyrimidines were planned in order to study the effects of the 5-substitution with alkoxy/phenoxy/alkylthio and phenylthio groups both on in vitro antiplatelet and in vivo antinociceptive activities. Antiplatelet activity was assessed in vitro against ADP, Arachidonic acid and U46619 induced aggregation, in rabbit plasma. Anti-inflammatory, analgesic and antipyretic activities were tested in rat paw edema, mouse writhing test and LPS induced rat fever, respectively. Amongst test compounds, 2-methylthio derivatives displayed an ASA-like antiplatelet activity whereas 2-methoxy and, particularly, 2-methanesulfonyl derivatives showed a broad spectrum of antiplatelet action, inhibiting both the ADP- and the AA- and U46619-induced aggregation. With regard to the in vivo pharmacological activities, mainly the 2-methoxy derivatives showed a significant analgesic effect comparable to that of indomethacin. SAR considerations, also in comparison with a number of previously described compounds, were performed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.018
• 作为产物：
  描述：

  甲醇 、 2-methylthio-5-hydroxy-5H-[1]benzopyrano[4,3-d]pyrimidine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以68%的产率得到10-Methoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 5H-[1]benzopyrano[4,3-d]pyrimidines effective as antiplatelet/analgesic agents

  摘要：

  Synthesis and pharmacological screening of new2-methylthio/2-methanesulfonyl/2-methoxy-5H-[1]benzopyrano[4,3-d]pyrimidines were planned in order to study the effects of the 5-substitution with alkoxy/phenoxy/alkylthio and phenylthio groups both on in vitro antiplatelet and in vivo antinociceptive activities. Antiplatelet activity was assessed in vitro against ADP, Arachidonic acid and U46619 induced aggregation, in rabbit plasma. Anti-inflammatory, analgesic and antipyretic activities were tested in rat paw edema, mouse writhing test and LPS induced rat fever, respectively. Amongst test compounds, 2-methylthio derivatives displayed an ASA-like antiplatelet activity whereas 2-methoxy and, particularly, 2-methanesulfonyl derivatives showed a broad spectrum of antiplatelet action, inhibiting both the ADP- and the AA- and U46619-induced aggregation. With regard to the in vivo pharmacological activities, mainly the 2-methoxy derivatives showed a significant analgesic effect comparable to that of indomethacin. SAR considerations, also in comparison with a number of previously described compounds, were performed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.018

文献信息

• Synthesis and pharmacological evaluation of 5H-[1]benzopyrano[4,3-d]pyrimidines effective as antiplatelet/analgesic agents
  作者：Olga Bruno、Chiara Brullo、Silvia Schenone、Francesco Bondavalli、Angelo Ranise、Massimiliano Tognolini、Vigilio Ballabeni、Elisabetta Barocelli

  DOI：10.1016/j.bmc.2003.11.018

  日期：2004.2

  Synthesis and pharmacological screening of new2-methylthio/2-methanesulfonyl/2-methoxy-5H-[1]benzopyrano[4,3-d]pyrimidines were planned in order to study the effects of the 5-substitution with alkoxy/phenoxy/alkylthio and phenylthio groups both on in vitro antiplatelet and in vivo antinociceptive activities. Antiplatelet activity was assessed in vitro against ADP, Arachidonic acid and U46619 induced aggregation, in rabbit plasma. Anti-inflammatory, analgesic and antipyretic activities were tested in rat paw edema, mouse writhing test and LPS induced rat fever, respectively. Amongst test compounds, 2-methylthio derivatives displayed an ASA-like antiplatelet activity whereas 2-methoxy and, particularly, 2-methanesulfonyl derivatives showed a broad spectrum of antiplatelet action, inhibiting both the ADP- and the AA- and U46619-induced aggregation. With regard to the in vivo pharmacological activities, mainly the 2-methoxy derivatives showed a significant analgesic effect comparable to that of indomethacin. SAR considerations, also in comparison with a number of previously described compounds, were performed. (C) 2003 Elsevier Ltd. All rights reserved.