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

Authors

ROBABEH KAVIANI
MINA SAEEDI
MOHAMMAD MAHDAVI
HAMIND NADRI
ALIREZA MORADI
ABBAS SHAFIEE
TAHMINEH AKBARZADEH

DOI

10.3906/kim-1604-13

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-2$H$-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/NH$_{4}$Cl 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-2$H$-chromen-7-yl)oxy)phenyl)carbamothioyl)benzamide (7l) showed the best activity as potent as the reference drug, quercetin.

Keywords

Chromenone, nitro compounds, $N$-carbamothioyl, soybean 15-LOX

First Page

335

Last Page

344

Recommended Citation

KAVIANI, ROBABEH; SAEEDI, MINA; MAHDAVI, MOHAMMAD; NADRI, HAMIND; MORADI, ALIREZA; SHAFIEE, ABBAS; and AKBARZADEH, TAHMINEH (2017) "Synthesis of novel derivatives of chromenone bearing an $N$-carbamothioyl moiety as soybean 15-LOX inhibitors," Turkish Journal of Chemistry: Vol. 41: No. 3, Article 3. https://doi.org/10.3906/kim-1604-13
Available at: https://journals.tubitak.gov.tr/chem/vol41/iss3/3