4-Aminoantipyrine in carbohydrate research: Design, synthesis and anticancer activity of thioglycosides of a novel class of 4-aminoantipyrines and their corresponding pyrazolopyrimidine and pyrazolopyridine thioglycosides

5 years ago

4-Aminoantipyrine in carbohydrate research: Design, synthesis and anticancer activity of thioglycosides of a novel class of 4-aminoantipyrines and their corresponding pyrazolopyrimidine and pyrazolopyridine thioglycosides

A convenient method for the synthesis of antipyrine, pyrazolopyrimidine and pyrazolopyridine thioglycosides was developed. This study reports a novel and efficient method for the synthesis of thioglycosides of a novel class of 4-aminoantipyrines 6a,b; 13a,b and their corresponding pyrazolopyrimidine thioglycosides 7a,b; 9a,b and pyrazolopyridine thioglycosides 14a,b; 16a,b. These series of compounds were designed through the reaction of sodium cyanocarbonimidodithioate 2 and sodium 2,2-dicyanoethene-1,1-bis(thiolate) 10 with 4-aminoantipyrine 1. Ammonolysis of the thioglycosides 6, 7, 13, 14 afforded the corresponding free thioglycosides 8, 9, 15, 16. The scope and limitation of the method is demonstrated. The structures of the reaction products were determined based on their initial analysis and spectroscopic data (¹³C NMR, IR, MS, ¹H NMR). The antitumor activity of the synthesized compounds against human cancer cell lines has been tested; liver (HEPG2), breast (MCF-7) and colon (HCT116). In general, the synthesized compounds displayed a moderate antitumor activity, compound 9b was the most cytotoxic drug, inhibiting replication of human liver cancer cells in vitro, while compound 7b was promising as it affected two types of human cancer cells (liver cancer and colon cancer).

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DOI: S0040402017308554