Abstract
Current research is based on the synthesis of novel (E)-4-aryl-2-(2-(pyren-1-ylmethylene)hydrazinyl)thia zole derivatives (3-15) by adopting two steps route. First step was the condensation between the pyrene-1-carbaldehyde (1) with the thiosemicarbazide to afford pyrene-1-thiosemicarbazone intermediate (2). While in second step, cyclization between the intermediate (2) and phenacyl bromide derivatives or 2-bromo ethyl acetate was carried out. Synthetic derivatives were structurally characterized by spectroscopic techniques such as EI-MS, H-1 NMR and C-13 NMR. Stereochemistry of the iminic double bond was confirmed by NOESY analysis. All pure compounds 2-15 were subjected for in vitro beta-glucuronidase inhibitory activity. All molecules were exhibited excellent inhibition in the range of IC50 = 3.10 +/- 0.10-40.10 +/- 0.90 mu M and found to be even more potent than the standard D-saccharic acid 1,4-lactone (IC50 = 48.38 +/- 1.05 mu M). Molecular docking studies were carried out to verify the structure-activity relationship. A good correlation was perceived between the docking study and biological evaluation of active compounds. (C) 2016 Elsevier Inc. All rights reserved.