4-chloro-8-methyl-7-(3-pyridylmethoxy)-2H-1-benzopyran-2-one | 714961-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-chloro-8-methyl-7-(3-pyridylmethoxy)-2H-1-benzopyran-2-one
• 英文别名: 4-Chloro-8-methyl-7-(pyridin-3-ylmethoxy)chromen-2-one
• CAS: 714961-34-9
• 化学式: C₁₆H₁₂ClNO₃
• 分子量: 301.729
• InChiKey: BQYVWRLBGPZXGU-UHFFFAOYSA-N

物化性质

• 熔点：
  222 °C(Solv: dichloromethane (75-09-2); ethyl acetate (141-78-6))
• 沸点：
  491.7±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌嗪 、 4-chloro-8-methyl-7-(3-pyridylmethoxy)-2H-1-benzopyran-2-one 以 乙醇 为溶剂， 反应 2.0h， 以79%的产率得到8-methyl-4-(1-piperazinyl)-7-(3-pyridinylmethoxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins

  摘要：

  Pursuing our chemical and biological studies in this field, we described the multistep preparation of the new 5-, 6-, or 7-alkoxy and 7-alkoxy-8-methyl substituted 4-(1-piperazinyl)coumarins 5d-v, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187. Compounds 5h-j,p,r-u showed notably high activity towards all the platelet aggregation inducers used, and the most active one, 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin (5t), proved to be a potent in vitro antiplatelet agent. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.010
• 作为产物：
  描述：

  3-氯甲基吡啶盐酸盐 在 氢氧化钾 、 sodium 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 二苯醚 、 丁酮 、 xylene 为溶剂， 反应 7.33h， 生成 4-chloro-8-methyl-7-(3-pyridylmethoxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis and in vitro inhibitory activity on human platelet aggregation of novel properly substituted 4-(1-piperazinyl)coumarins

  摘要：

  Pursuing our chemical and biological studies in this field, we described the multistep preparation of the new 5-, 6-, or 7-alkoxy and 7-alkoxy-8-methyl substituted 4-(1-piperazinyl)coumarins 5d-v, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187. Compounds 5h-j,p,r-u showed notably high activity towards all the platelet aggregation inducers used, and the most active one, 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin (5t), proved to be a potent in vitro antiplatelet agent. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.010

文献信息

• Synthesis and In Vitro Antiplatelet Activity of New 4-(1-Piperazinyl)coumarin Derivatives. Human Platelet Phosphodiesterase 3 Inhibitory Properties of the Two Most Effective Compounds Described and Molecular Modeling Study on Their Interactions with Phosphodiesterase 3A Catalytic Site
  作者：Giorgio Roma、Mario Di Braccio、Giancarlo Grossi、Daniela Piras、Giuliana Leoncini、Debora Bruzzese、Maria Grazia Signorello、Paola Fossa、Luisa Mosti

  DOI：10.1021/jm0611511

  日期：2007.6.1

  The synthesis and in vitro antiplatelet activity significant data of coumarin derivatives 5i-x and quinolin-2(1H)-one derivatives 22a,b, as well as the corresponding structure-activity relationships are described. The recently reported 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin 5f and its potent 7-(2-morpholinoethoxy)-substituted new analogue 5u were notably more effective inhibitors of pure human platelet PDE3 than milrinone and cilostazol: these data were related, through a molecular modeling study, with the molecular interactions of the four compounds with the human PDE3A catalytic site.