Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones

• Published in: Bioorganic and Medicinal Chemistry
• Main Author: Khan K.M.; Saad S.M.; Shaikh N.N.; Hussain S.; Fakhri M.I.; Perveen S.; Taha M.; Choudhary M.I.
• Format: Article
• Language: English
• Published: Elsevier Ltd 2014
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84901927895&doi=10.1016%2fj.bmc.2014.04.039&partnerID=40&md5=0e2ea5b060a41cd08faa053639f44ecd
• ISSN: 09680896
• DOI: 10.1016/j.bmc.2014.04.039

2-Arylquinazolin-4(3H)-ones 1-25 were synthesized by reacting anthranilamide with various benzaldehydes using CuCl2·2H 2O as a catalyst in ethanol under reflux. Synthetic 2-arylquinazolin-4(3H)-ones 1-25 were evaluated for their β-glucuronidase inhibitory potential. A trend of inhibition IC50 against the enzyme in the range of 0.6-198.2 μM, was observed and compared with the standard d-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM). Compounds 13, 19, 4, 12, 14, 22, 23, 25, 15, 8, 17, 11, 21, 1, 3, 18, 9, 2, and 24 with the IC50 values within the range of 0.6-44.0 μM, indicated that the compounds have superior activity than the standard. The compounds showed no cytotoxic effects against PC-3 cells. A structure-activity relationship is established. © 2014 Elsevier Ltd. All rights reserved.