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

Synthesis and anticancer activity of some new heterocyclic compounds based on... 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. Research on Chemical Intermediates Springer Journals

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

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Springer Netherlands
Copyright © 2015 by Springer Science+Business Media Dordrecht
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
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