Synthesis of novel derivatives of chromenone bearing an N-carbamothioyl moiety as soybean 15-LOX inhibitors

Abstract

Novel derivatives of chromenone bearing an N-carbamothioyl moiety were synthesized and evaluated for their soybean 15-LOX inhibitory activity. Synthesis of the target compounds was started from 7-hydroxy-2H-chromen-2-one. It was reacted with 1-fluoro-2(4)-nitrobenzene to obtain the corresponding nitrophenoxy-chromenone derivative. Reduction of the nitro group was achieved in the presence of Zn/NH4Cl and reaction of the latter compound with in situ prepared benzoyl isothiocyanate led to the formation of the title compounds. All compounds were characterized and tested against soybean 15-LOX. Among them, 4-methyl-N-((4-((2-oxo-2H-chromen-7-yl)oxy)phenyl)carbamothioyl)benzamide (7l) showed the best activity as potent as the reference drug, quercetin.