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Research on Chemical Intermediates

, Volume 42, Issue 2, pp 1071–1089 | Cite as

Synthesis and anticancer activity of some new heterocyclic compounds based on 1-cyanoacetyl-3,5-dimethylpyrazole

  • Nadia H. MetwallyEmail author
  • Fathy M. Abdelrazek
  • Salwa M. Eldaly
Article

Abstract

The starting 3-(3,5-dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrile (1) reacts with phenyl isothiocyanate and ethyl bromoacetate to give the corresponding thiazole derivative 4. On repetition of the reaction using phenacyl bromides 5a–d (instead of ethyl bromoacetate), oxathiepine-6-carbonitriles 10a–d were obtained. Coupling of compound 1 with aryldiazonium chlorides gives the corresponding 2-(arylhydrazono)-(3,5-dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrile derivatives 12a–e, which on treatment with p-phenylenediamine, followed by reaction of hydrazine hydrate afforded pyrazole derivatives 15a–d. The reaction of 1 with 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile afforded the respective 2-cyanomethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivative 18. Compound 18 reacted with phenyl isothiocyanate in the presence of potassium hydroxide at room temperature and then phenacyl bromide was added; the pyrazolopyrimidines 24 were obtained. The structures of all the newly synthesized products were confirmed based on elemental, spectral data and a plausible mechanism has been postulated to account for their formation. Also, we evaluate the anticancer activity of some representative examples of the newly synthesized compounds.

Keywords

3-(35-dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrile Oxathiepine-6-carbonitriles Pyrazolo-[1,5-a]pyrimidine Thiazoles Anticancer activity 

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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Nadia H. Metwally
    • 1
    Email author
  • Fathy M. Abdelrazek
    • 1
  • Salwa M. Eldaly
    • 1
  1. 1.Chemistry Department, Faculty of ScienceCairo UniversityGizaEgypt

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