10-Ethoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene | 677032-55-2

• 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-Ethoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene
• 英文别名: 5-ethoxy-2-methylsulfanyl-5H-chromeno[4,3-d]pyrimidine
• CAS: 677032-55-2
• 化学式: C₁₄H₁₄N₂O₂S
• 分子量: 274.343
• InChiKey: RTSSKIJAGZCLHO-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C(Solv: ethanol (64-17-5))
• 沸点：
  461.8±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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-Ethoxy-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69%的产率得到10-Ethoxy-3-methanesulfonyl-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：

  2-methylthio-5H-[1]benzopyrano[4,3-d]pyrimidin-5-piperidine hydrochloride 以 乙醇 为溶剂， 生成 10-Ethoxy-3-methylsulfanyl-10H-9-oxa-2,4-diaza-phenanthrene
  参考文献：
  名称：

  New polycyclic pyrimidine derivatives with antiplatelet in vitro activity: synthesis and pharmacological screening

  摘要：

  The preparation and the pharmacological screening of novel anti-aggregatory/antiphlogistic polycyclic pyrimidine derivatives are described. The compounds were developed starting from bioactive 2-aminobenzopyranopyrimidine derivatives in order to assess the importance of the benzopyrano[4,3-d]pyrimidine structure and the role of an amino basic moiety in position 2. Antiplatelet activity was assessed in vitro against ADP and arachidonic acid-induced aggregation in guinea-pig plasma. Anti-inflammatory analgesic/antipyretic activities were studied in rat paw oedema, mouse writhing test and E coli-induced rat fever. Ulcerogenic and gastroprotective effects were also investigated in vivo on rat gastric mucosa. Among the tested compounds, the 5-substituted benzopyranopyrimidine derivatives 3d and 4d proved to be the most active antiplatelet agents as potent as acetylsalicylic acid against arachidonic acid-stimulated aggregation. Furthermore the 2-methylthio derivative 4d was endowed with greater efficacy against ADP aggregation suggesting that additional non-TXA(2) dependent mechanisms are involved in its biological activity. Orally administered at 100 mg kg(-1) in rats this latter compound displayed antiphlogistic acitivity comparable to indomethacin (10 mg kg(-1)) coupled with an unusual gastroprotective effect on ethanol-induced ulcers. In conclusion, these findings indicate that the 5-pyrrolidino-2-methylthiobenzopyrano[4d] fulfils the chemical requirements to exhibit antiplatelet activity associated with gastroprotective effect. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00272-8