Pyrazolo[1,5-a]pyridin-3-yl-pyridin-3-yl-methanone | 111253-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: Pyrazolo[1,5-a]pyridin-3-yl-pyridin-3-yl-methanone
• 英文别名: Pyrazolo[1,5-a]pyridin-3-yl(pyridin-3-yl)methanone
• CAS: 111253-43-1
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: NLQDLANZDHQUAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯化烟碱盐酸盐 、 2-methylpyrazolo<1,5-α>pyridine 以23%的产率得到
  参考文献：
  名称：

  AWANO KATSUYA; SUZUE SEIGO; SEGAWA MITSURU, CHEM. AND PHARM. BULL., 34,(1986) N 7, 2828-2832

  摘要：

  DOI：

文献信息

• Synthesis of 3-substituted pyrazolo(1,5-a)pyridine derivatives with inhibitory activity on platelet aggregation. I.
  作者：KATSUYA AWANO、SEIGO SUZUE、MITSURU SEGAWA

  DOI：10.1248/cpb.34.2828

  日期：——

  3-Nicotinoylpyrazolo[1, 5-a]pyridines were synthesized by the raation of 3-unsubstituted pyrazolo[1, 5-a]pyridines with nicotinoyl chloride hydrochloride. Tetrahydronicotinoyl derivatives were obtained by hydrogenation of the nicotinoyl derivatives. Furthermore, N-substituted derivatives were synthesized by the reaction of the tetrahydronicotinoyl derivatives with alkylating regents or isocyanates. These pyrazolo[1, 5-a]pyridines were tested for inhibitory activity on arachidonic acid induced platelet aggregation in vitro and ex vivo. Some of these compounds showed higher inhibitory activity than aspirin. Among them, 2-methyl-3-(1, 4, 5, 6-tetrahydronicotinoyl)pyrazolo[1, 5-a]pyridine was found to be the most active compound.

  3- 未取代的吡唑并[1, 5-a]吡啶与烟酰氯盐酸盐反应合成了 3-烟酰基吡唑并[1, 5-a]吡啶。通过对烟碱酰氯衍生物进行氢化，得到了四氢烟碱酰氯衍生物。此外，通过四氢烟酰衍生物与烷基化调节剂或异氰酸酯的反应，还合成了 N-取代衍生物。这些吡唑并[1, 5-a]吡啶在体外和体内测试了对花生四烯酸诱导的血小板聚集的抑制活性。其中一些化合物的抑制活性高于阿司匹林。其中，2-甲基-3-（1，4，5，6-四氢烟酰）吡唑并[1，5-a]吡啶被认为是活性最强的化合物。