2-benzoyloxy-5-chloro-3-[4-(methylthio)phenyl]pyridine | 745050-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-benzoyloxy-5-chloro-3-[4-(methylthio)phenyl]pyridine
• 英文别名: 2-(Benzyloxy)-5-chloro-3-[4-(methylsulfanyl)phenyl]pyridine；5-chloro-3-(4-methylsulfanylphenyl)-2-phenylmethoxypyridine
• CAS: 745050-28-6
• 化学式: C₁₉H₁₆ClNOS
• 分子量: 341.861
• InChiKey: AZPQDBGVWLDQRS-UHFFFAOYSA-N

物化性质

• 沸点：
  454.8±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoyloxy-5-chloro-3-[4-(methylthio)phenyl]pyridine 在 四(三苯基膦)钯 、 三氟乙酸 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 5-氯-3-(4-甲基磺酰基)苯基-2-(2-甲基-5-吡啶基)吡啶
  参考文献：
  名称：

  Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx® and Arcoxia®

  摘要：

  The preparation of the sulfoxide analogues 2 and 4, and their enantiomeric pure forms is discussed as well as their potential to act as prodrugs to the potent and selective sulfone-containing COX-2 inhibitors rofecoxib and etoricoxib. Sulfoxides 2 and 4 were shown to be effectively transformed in vivo into rofecoxib and etoricoxib, respectively, after oral administration in rats. In the case of sulfoxide 2, both a slightly improved pharmacokinetic profile and a better pharmacological activity in an arthritis model were seen when compared with rofecoxib. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.052
• 作为产物：
  描述：

  3-溴-5-氯-2-苯基甲氧基吡啶 、 4-甲硫基苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 以88%的产率得到2-benzoyloxy-5-chloro-3-[4-(methylthio)phenyl]pyridine
  参考文献：
  名称：

  [EN] 2,3'-BIPYRIDINES DERIVATIVES AS SELECTIVE COX-2 INHIBITORS
  [FR] DERIVES DE 2,3'-BIPYRIDINES SERVANT D'INHIBITEURS DE COX-2 SELECTIFS

  摘要：

  本发明涉及式(I)的2,3'-联吡啶。它们的制备方法、含有它们的药物组合物以及它们的医药用途。

  公开号：

  WO2004072037A1

文献信息

• 2,3'-bipyridines derivatives as selective cox-2 inhibitors
  申请人：Caturla Javaloyes Francisco Juan

  公开号：US20060229338A1

  公开（公告）日：2006-10-12

  The present invention relates to 2,3′-bipyridines of formula (I), processes for their preparation, pharmaceutical compositions containing them, and their medical uses.

  本发明涉及式(I)的2,3'-联吡啶，其制备方法，含有它们的药物组合物及其医药用途。
• 2,3 -BIPYRIDINES DERIVATIVES AS SELECTIVE COX-2 INHIBITORS
  申请人：Almirall Prodesfarma, S.A.

  公开号：EP1592666A1

  公开（公告）日：2005-11-09
• [EN] 2,3'-BIPYRIDINES DERIVATIVES AS SELECTIVE COX-2 INHIBITORS<br/>[FR] DERIVES DE 2,3'-BIPYRIDINES SERVANT D'INHIBITEURS DE COX-2 SELECTIFS
  申请人：ALMIRALL PRODESFARMA SA

  公开号：WO2004072037A1

  公开（公告）日：2004-08-26

  The present invention relates to 2,3'-bipyridines of formula (I). Processes for their preparation, pharmaceutical compositions containing them, and their medical uses.

  本发明涉及式(I)的2,3'-联吡啶。它们的制备方法、含有它们的药物组合物以及它们的医药用途。
• Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx® and Arcoxia®
  作者：Francisco Caturla、Mercè Amat、Raquel F. Reinoso、Mónica Córdoba、Graham Warrellow

  DOI：10.1016/j.bmcl.2006.03.052

  日期：2006.6

  The preparation of the sulfoxide analogues 2 and 4, and their enantiomeric pure forms is discussed as well as their potential to act as prodrugs to the potent and selective sulfone-containing COX-2 inhibitors rofecoxib and etoricoxib. Sulfoxides 2 and 4 were shown to be effectively transformed in vivo into rofecoxib and etoricoxib, respectively, after oral administration in rats. In the case of sulfoxide 2, both a slightly improved pharmacokinetic profile and a better pharmacological activity in an arthritis model were seen when compared with rofecoxib. (c) 2006 Elsevier Ltd. All rights reserved.