Synthesis, enzyme inhibition and anticancer investigations of unsymmetrical 1,3-disubstituted ureas

Abstract

In this study, seventeen urea derivatives, including the five new derivatives N-mesityl-N'-(3-methylphenyl)urea (2), N-(3-methoxyphenyl)-N'- -(3-methylphenyl)urea (4), N-mesityl-N'-(4-methylphenyl)urea (6), N-(1,3-benzothiazol- 2-yl)-N'-(3-methylphenyl)urea (9) and N-(2-methylphenyl)-2- oxo-1- -pyrrolidinecarboxamide (15), were synthesized by reacting ortho-, meta- and para-tolyl isocyanate with primary and secondary amines using a previously reported method. All the series 1-17 were subjected to urease, β-glucuronidase and snake venom phosphodiesterase enzyme inhibition assays. The ranges of inhibition of urease, β-glucuronidase and phosphodiesterase enzymes were 0.30-45.3, 4.9-44.9 and 1.2-46.4 %, respectively. Moreover, an effect of these compounds on a prostate cancer cell line was observed. The new compound N-(1,3-benzothiazol-2-yl)-N'-(3-methylphenyl)urea (9) showed in vitro anticancer activity with an IC50 value of 78.28±1.2 μM. All the compounds were characterized by state of art spectroscopic techniques.©2014 SCS.