Mlakić, Milena; Đurčević, Ema; Odak, Ilijana; Barić, Danijel; Juričević, Ines; Šagud, Ivana; Burčul, Franko; Lasić, Zlata; Marinić, Željko; Škorić, Irena (2023) Thieno-thiazolostilbenes, thienobenzo-thiazoles and naphtho-oxazoles: Computational study and cholinesterase inhibitory activity. Molecules, 28 (9). ISSN 1420-3049
|
PDF
- Published Version
- article
Available under License Creative Commons Attribution. Download (1MB) | Preview |
Abstract
Naphtho-triazoles and thienobenzo-triazoles have so far proven to be very potent inhibitors of the enzyme butyrylcholinesterase (BChE). Based on these results, in this work, new thienobenzo- thiazoles were designed and synthesized, and their potential inhibitory activity was tested and compared with their analogs, naphtho-oxazoles. The synthesis was carried out by photochemical cyclization of thieno-thiazolostilbenes obtained in the first reaction step. Several thienobenzo- thiazoles and naphtho-oxazoles have shown significant potential as BChE inhibitors, together with the phenolic thiazolostilbene being the most active of all tested compounds. These results are significant as BChE has been attracting growing attention due to its positive role in the treatment of Alzheimer's disease. Computational examination based on the DFT approach enabled the characterization of the geometry and electronic structure of the studied molecules. Furthermore, the molecular docking study, accompanied by additional optimization of complexes ligand-active site offered insight into the structure and stabilizing interactions in the complexes of studied molecules and BChE.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | cholinesterase inhibition ; electronic structure ; molecular docking ; 1, 3-oxazole ; thiophene ; 1, 3-thiazole |
| Subjects: | NATURAL SCIENCES > Chemistry |
| Divisions: | Division of Physical Chemistry |
| Depositing User: | Danijela Barić |
| Date Deposited: | 21 Jun 2023 11:53 |
| URI: | http://fulir.irb.hr/id/eprint/8059 |
| DOI: | 10.3390/molecules28093781 |
Actions (login required)
 |
View Item |
Altmetric
Altmetric
