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

摘要

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 15a–c were treated with various amino acids (16a–h) to obtain benzenesulphonamide derivatives 17a–l. Compounds 17a–f were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives 19a–f. Further reactions of compounds 19a–f and 17g–l with 4- or 2-aminopyrimidine (20) using boric acid as a catalyst gave the required sulphonamide carboxamide derivatives 21a–q 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 21a–c, 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.