S. Elgogary, Rizk E. Khidre, E. M. El-Telbani
Feb 17, 2020
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Journal
Journal of the Iranian Chemical Society
Abstract
A novel series of 1,2,3-triazole containing sulfonamide moiety was synthesized. Treatment of 4-acetyl 1,2,3-triazole 3 with different aldehydes gave α , β -unsaturated ketones 4a – c . Condensation of 3 with dimethylformamide dimethylacetal (DMF-DMA) gave formimidamide 5 . Chalcone 7 was achieved via two ways from the reaction of 5 with benzaldehyde or from treatment of 4a with DMF-DMA. Reaction of 7 with hydrazine hydrate afforded pyrazoline 8 . 5-Methyl pyrazole 12 was synthesized from Claisen condensation reaction of 3 or 5 with ethyl acetate to give 1,3-diketone adduct 9 or 10 , respectively, followed by treatment with hydrazine hydrate. 5-Aminopyrazole 17 was synthesized from the reaction of ester 13 or formimidamide ester 13a with acetonitrile to afford cyanoacetyl derivatives 14 or 15 , respectively, followed by treatment with hydrazine hydrate. The new compounds were screened for their in vitro antitumor activity. The results of this investigation revealed that compounds 12 , 7 , and 17 had a significant anticancer activity against MCF-7 cancer cell line with IC 50 values 12.4, 19.8, and 23.4 µM, respectively, in relation to the standard drug, doxorubicin.