Synthesis and in vitro anticancer activity of pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-d][1,2,3]triazines |
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| Authors: | Ashraf S Hassan Gaber O Moustafa Hanem M Awad |
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| Institution: | 1. Department of Organometallic and Organometalloid Chemistry, National Research Centre, Cairo, Egyptashraf_salmoon@yahoo.com;3. Department of Peptide Chemistry, National Research Centre, Cairo, Egypt;4. Department of Tanning Materials and Leather Technology, National Research Centre, Cairo, Egypt |
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| Abstract: | A novel series of pyrazolo1,5-a]pyrimidines 14a–j and pyrazolo1,5-a]quinazolines 18a, b were synthesized via condensation of 5-amino-1H-pyrazoles 10a, b with 3-(dimethylamino)-1-aryl-prop-2-en-1-ones 11a–e and 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione (15), respectively, in glacial acetic acid. Finally, treatment of 10a, b with sodium nitrite (NaNO2) afforded pyrazolo3,4-d]triazines 20a, b. Structures of compounds were confirmed by their spectral data. These compounds were screened for their in vitro cytotoxic activities against human cancer cell lines (HepG-2 and MCF-7) using 3-4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. The results reveal that, the compounds 14b and 14h were the most potent in comparison with doxorubicin. The structure–activity relationship was discussed. |
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| Keywords: | 5-Aminopyrazole anticancer activity fused pyrazoles pyrazolo[1 5-a]pyrimidines pyrazolo[1 5-a]quinazolines pyrazolo[3 4-d]triazines |
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