- Turkish Journal of Chemistry
- Vol: 42 Issue: 4
- Synthesis, molecular docking, and pharmacological evaluation of halobenzodithiophene derivatives aga...
Synthesis, molecular docking, and pharmacological evaluation of halobenzodithiophene derivatives against alpha-glucosidase, urease, and free radical production
Authors : Ghulam Abbas, Zahid Hassan, Ahmed Al-harrasi, Syed Aun Muhamaad, Ahood Juma Al-quraini, Zahra Khamis Al-maani, Ahmed Mohammed Al-adawai
Pages : 1113-1123
View : 11 | Download : 9
Publication Date : 9999-12-31
Article Type : Makaleler
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 ( 1 ) exhibited potent activity with IC 50 50 = 135 ± ± 0.51 μ μ M, while its derivative 2,7-bis(butoxycarbonyl)-3,6-dichlorobenzo[1,2- b b ;6,5- b b ']dithiophene ( 2 ) exhibited promising inhibition with IC 50 50 = 263 ± ± 0.32 μ μ M. In the 1,1-diphenyl-2-picrylhydrazyl (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 (butoxycarbonyl)-3,6-dichlorobenzo[1,2- b b ;6,5- b b '] dithiophene ( 1 ) containing two chlorine substitutions exhibited more alpha-glucosidase inhibition (IC 50 50 = 263 ± ± .0.32 μ μ M) than other derivatives. Moreover, compound 2,7-bis (butoxycarbonyl)-3,6-dichlorobenzo[1,2- b b ;6,5- b b '] dithiophene ( 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, structure–activity relationship