Synthesis of chalcone-imide derivatives and investigation of their anticancer and antimicrobial activities, carbonic anhydrase and acetylcholinesterase enzymes inhibition profiles

• Published in: Archives of physiology and biochemistry Vol. 124; no. 1; pp. 61 - 68
• Main Authors: Kocyigit, Umit Muhammet, Budak, Yakup, Gürdere, Meliha Burcu, Ertürk, Fatih, Yencilek, Belkız, Taslimi, Parham, Gülçin, İlhami, Ceylan, Mustafa
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.01.2018
• Subjects: acetylcholinesterase; anticancer activity; antimicrobial activity; carbonic anhydrase; Chalcone-imide; carbonic anhydrase; acetylcholinesterase; Chalcone-imide; anticancer activity; antimicrobial activity
• ISSN: 1381-3455; 1744-4160; 1744-4160
• DOI: 10.1080/13813455.2017.1360914

The new 1-(4-(3-(aryl)acryloyl)phenyl)-1H-pyrrole-2,5-diones (5a-g) were prepared from 4′-aminchalcones (3a-g) and screened for biological activities. All compounds (3a-g and 5a-g), except 3d and 3e displayed good cytotoxic activities with IC 50 values in the range of 7.06-67.46 μM. IC 50 value of 5-fluorouracil (5-FU) was 90.36 μM. Moreover, most of compounds 5a-g showed high antibacterial activity with 8-20 mm of inhibition zone (19-25 mm of Sulbactam-Cefoperazone (SCF)). In addition, they showed good inhibitory action against acetylcholinesterase (AChE), and human carbonic anhydrase I, and II (hCA I and hCA II) isoforms. Also, these compounds demonstrated effective inhibition profiles with Ki values of 426.47-699.58 nM against hCA I, 214.92-532.21 nM against hCA II, and 70.470-229.42 nM against AChE. On the other hand, acetazolamide, clinically used drug, showed a Ki value of 977.77 ± 227.4 nM against CA I, and 904.47 ± 106.3 nM against CA II, respectively. Also, tacrine inhibited AChE showed a Ki value of 446.56 ± 58.33 nM.