Synthesis and biological evaluation of new pyrazolo[3,4-d]pyrimidine derivatives

Authors

  • Asma Agrebi Laboratory of Applied Chemistry HCGP, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia.
  • Fatma Allouche Laboratory of Applied Chemistry HCGP, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia.
  • Hamadi Fetoui Laboratory of Toxicology-Microbiology and Environmental Health (11ES70), Faculty of Science, University of Sfax, 3000 Sfax, Tunisia.
  • Fakher Chabchoub Laboratory of Applied Chemistry HCGP, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia.

DOI:

https://doi.org/10.13171/mjc.3.2.2014.13.05.23

Abstract

Several new pyrazolopyrimidine compounds were achieved from aminocyanopyarazole 1. The starting material 1 was initially coupled with orthoester at refluxed with various primary amines, ammonia, hydrazines and hydroxylamine to furnish a series of pyrazolo[3,4-d]pyrimidines. The reaction of imidate 2a-b with hydrazide derivatives led to the formation of pyrazolo[3,4-d][1,2,4]triazolo[4,3-c]pyrimidines. Some of the synthesized compounds 3a and 4c were evaluated for their anti-inflammatory, antipyretic and nociceptive activities. We start by studing the toxicity of these two molecules by measuring the corresponding DL50. The DL50 of 3a and 4c are estimated to 1333.2mg / kg and 1593.5mg / kg respectively. Pharmacological evaluation showed that compounds 3a and 4c at doses (5.5-22.2 mg / Kg, i.p) exhibited anti-inflammatory activities compared to Ibuprofen (150 mg / Kg, i.p), used as a refer ence drug. Further, our study showed that the injection of derived pyrazolopyrimidines on hyperthermic animal leads to a decrease in temperature after 1 hours of treatment compared to paracetamol used as reference. In addition, the injection of derived pyrazolopyrimidines at different doses contains a potent nociceptive activity. This effect is dose-dependent compared to aspirin.

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Published

2014-05-13

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Organic Chemistry