Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties

David Izuchukwu Ugwu, Uchechukwu C. Okoro, Narendra Kumar Mishra


Pyrimidines, sulphonamides and carboxamides have shown a large number of pharmacological properties against different types of diseases inc­luding helminthiasis. Seventeen new pyrimidine derivatives bearing sulphon­amide and carboxamide were synthesized and investigated for their in vitro anthelmintic properties. Substituted benzenesulphonyl chlorides 15ac were treated with various amino acids (16ah) to obtain benzenesulphonamide derivatives 17al. Compounds 17af were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives 19af. Further reactions of compounds 19af and 17gl with 4- or 2-aminopyrimidine (20) using boric acid as a catalyst gave the required sulphonamide carboxamide derivatives 21aq in excellent yields. The compounds were isolated in their analytical grade and characterized using FTIR, 1H-NMR, 13C-NMR and HRMS. The in vitro anthel­mintic studies showed that all the synthesized compounds possessed anthel­mintic property. Compounds 21ac, e, g, m and p showed mean paralyzing times of 15, 19, 14, 18, 19, 19 and 18 min, respectively, at 100 mg mL-1 compared to 10 min for albendazole. Compounds 21a–c, g and m had mean death times of 18, 24, 16, 20 and 25 min, respectively, at 100 mg mL-1 compared to 13 min for albendazole.


catalysis; anthelmintics; synthesis; carboxamides; sulphonamides


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