Synthesis, molecular docking, and pharmacological evaluation of halobenzodithiophene derivatives against alpha-glucosidase, urease, and free radical production

Authors : Ghulam ABBAS, Zahid HASSAN, Ahmed ALHARRASI, Syed Aun MUHAMAAD, Ahood Juma ALQURAINI, Zahra Khamis ALMAANI, Ahmed Mohammed ALADAWAI

Pages : 1113-1123

View : 14 | Download : 11

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Benzodithiophenes are heterocyclic compounds that have various medicinal and industrial applications. In the present study, halobenzodithiophene, the simplest benzofused thiophene, and its derivatives were synthesized and evaluated against alpha-glucosidase, urease, and free radical production. In the alpha-glucosidase inhibition assay, compound 2,2-bisbenzothiophne insert ignore into journalissuearticles values( 1 ); exhibited potent activity with IC 50 50 = 135 ± ± 0.51 μ μ M, while its derivative 2,7-bisinsert ignore into journalissuearticles values(butoxycarbonyl);-3,6-dichlorobenzo[1,2- b b ;6,5- b b `]dithiophene insert ignore into journalissuearticles values( 2 ); exhibited promising inhibition with IC 50 50 = 263 ± ± 0.32 μ μ M. In the 1,1-diphenyl-2-picrylhydrazyl insert ignore into journalissuearticles values(DPPH); radical-scavenging assay, compound 2 exhibited promising activity with IC 50 50 = 33 ± ± 0.42 μ μ M, while compound 1 showed moderate inhibition in the urease inhibition assay. Molecular docking studies determined the possible interaction of benzodithiophene and alpha-glucosidase on the basis of binding energy and scoring function. Structure-activity relationship analysis revealed that compound 2,7-bis insert ignore into journalissuearticles values(butoxycarbonyl);-3,6-dichlorobenzo[1,2- b b ;6,5- b b `] dithiophene insert ignore into journalissuearticles values( 1 ); containing two chlorine substitutions exhibited more alpha-glucosidase inhibition insert ignore into journalissuearticles values(IC 50 50 = 263 ± ± .0.32 μ μ M); than other derivatives. Moreover, compound 2,7-bis insert ignore into journalissuearticles values(butoxycarbonyl);-3,6-dichlorobenzo[1,2- b b ;6,5- b b `] dithiophene insert ignore into journalissuearticles values( 2 ); with two chlorine substitutions exhibited potent DPPH radical scavenging activity compared to other derivatives.
Keywords : Halobenzothiophenes, alpha glucosidase enzyme, urease enzyme, radical scavenging assay, molecular docking, structureactivity relationship