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

Abstract

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 IC₅₀ values in the range of 7.06–67.46 μM. IC₅₀ 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.

Keywords:

• Chalcone-imide
• anticancer activity
• antimicrobial activity
• acetylcholinesterase
• carbonic anhydrase

Disclosure statement

The authors declare that no conflicts of interest.

Additional information

Funding

Scientific and Technological Research Council of Turkey10.13039/501100004410111T990

The authors are indebted to the Scientific and Technological Research Council of Turkey [TUBİTAK Project No. 111T990] for financial supports.