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

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

Abstract


Pyrimidines, sulphonamides and carboxamides have shown large number of pharmacological properties against different types of diseases among which is helminthiasis. Seventeen new pyrimidine derivatives bearing sulphonamide and carboxamide were synthesized and investigated for their in vitro anthelmintic properties. The substituted benzenesulphonyl chlorides (15a-c) were treated with various amino acids (16a-h) to obtain the benzenesulphonamoyl alkanamides (17a-l). Compounds 17a-f were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives (19a-f). Further reactions of compound 19a-f, 17g-l with 4 or 2-aminopyrimidine (20) using boric acid as a catalyst gave the 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 synthesized compounds had anthelmintic property. Compounds 21a, 21b, 21c, 21e, 21g, 21m and 21p had mean paralyzing time of 15, 19, 14, 18, 19, 19 and 18 min at 100 mg/mL comparable to albendazole 10 min. Compounds 21a, 21b, 21c, 21g and 21m had mean death time of 18, 24, 16, 20, and 25 min at 100 mg/mL comparable to 13 min for albendazole.

Keywords


catalysis; anthelmintics; synthesis; carboxamides; sulphonamides

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DOI: http://dx.doi.org/10.2298/JSC170127109U

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