4-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one | 77494-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 4-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one
• 英文别名: 4-methylpyrazolo[1,5-a]pyrimidin-7-one
• CAS: 77494-09-8
• 化学式: C₇H₇N₃O
• 分子量: 149.152
• InChiKey: VTFVJLCBMVBAPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one 在 tetraphosphorus decasulfide 作用下， 以 吡啶 为溶剂， 反应 5.0h， 以46%的产率得到4-Methylpyrazolo[1,5-a]pyrimidine-7-thione
  参考文献：
  名称：

  Synthesis and antischistosomal activity of certain pyrazolo[1,5-a]pyrimidines

  摘要：

  Several 7-hydroxypyrazolo[1,5-a]pyrimidines (1-21), 7-mercaptopyrazolo[1,5-a]pyrimidines (37-49), and 4-alkylpyrazolo[1,5-a]pyrimidin-7-ones (50-55) and the corresponding 4-alkylpyrazolo[1,5-a]pyrimidine-7-thiones (56-60) were synthesized and tested for antischistosomal activity against Schistosoma mansoni. Of the compounds examined, the greatest degree of activity in vitro was found with the 7-mercaptopyrazolo[1,5-a]pyrimidines. In particular, compounds 37 and 47 proved lethal at 100 micrograms/mL after an exposure of only 1 h. The 7-hydroxypyrazolo[1,5-a]-pyrimidines were not as active. None of the compounds exhibiting in vitro activity were active against S. mansoni in vivo.

  DOI：

  10.1021/jm00137a023
• 作为产物：
  描述：

  ethyl 7-oxo-4H-pyrazolo[1,5-a]pyrimidine-6-carboxylate 在 sodium hydroxide 、 diphenyl ether-biphenyl eutectic 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-methylpyrazolo[1,5-a]pyrimidin-7(4H)-one
  参考文献：
  名称：

  吡唑并[1,5-α]嘧啶酮区域异构体的合成

  摘要：

  这项工作描述了制备吡唑并[1,5-α]嘧啶-7-ones的两种不同途径和两种制备吡唑并[1,5-α] pyrimidin-5-ones的途径。在制备嘧啶-5-酮区域异构体中使用1,3-二甲基尿嘧啶作为亲电子试剂代表了对先前报道结果的修正。另外，鉴定了制备该异构体的新反应并阐明了反应机理。这项工作为实验者提供了互补的合成途径，这些途径提供了嘧啶7-1或嘧啶5-5区域异构体。

  DOI：

  10.1021/jo062120g

文献信息

• 2-Phenylpyrazolo[1,5-a]pyrimidin-7-ones. A new class of nonsteroidal antiinflammatory drugs devoid of ulcerogenic activity
  作者：Gabriella Auzzi、Fabrizio Bruni、Lucia Cecchi、Annarella Costanzo、Lorenzo Pecori Vettori、Renato Pirisino、Marina Corrias、Giovanni Ignesti、Grazia Banchelli、Laura Raimondi

  DOI：10.1021/jm00366a009

  日期：1983.12

  Syntheses of some pyrazolo[1,5-a]pyrimidines were performed in order to study the relationship between structural modifications on the parent 4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one (1) and their antiinflammatory properties. The modifications carried out were introduction and functionalization of a longer side chain at the 4-position, substitution of the hydrogen atom at the 3-position, and replacement of the phenyl group with a 4-methylphenyl, methyl, or hydrogen substituent. 4-Ethyl-4,7-dihydro-2-phenylpyrazolo [1,5-a]pyrimidin-7-one (3) showed the highest activity and a better therapeutic index than phenylbutazone and indomethacin, used as reference drugs. All other changes at the 3-, 5-, and 6-positions, as well as the replacement of the phenyl group at position 2, caused a marked decrease of activity. Compound 3 was found devoid of ulcerogenic activity and was probably endowed with antiulcerogenic properties.
• SENGA, KEITARO;NOVINSON, T.;WILSON, H. R.;ROBINS, R. K., J. MED. CHEM., 1981, 24, N 5, 610-613
  作者：SENGA, KEITARO、NOVINSON, T.、WILSON, H. R.、ROBINS, R. K.

  DOI：——

  日期：——