Design, synthesis, biological evaluation and docking analysis of pyrrolidine-benzenesulfonamides as carbonic anhydrase or acetylcholinesterase inhibitors and antimicrobial agents
Por favor, use este identificador para citar o enlazar este ítem:
http://hdl.handle.net/10045/140467
Título: | Design, synthesis, biological evaluation and docking analysis of pyrrolidine-benzenesulfonamides as carbonic anhydrase or acetylcholinesterase inhibitors and antimicrobial agents |
---|---|
Autor/es: | Poyraz, Samet | Dondas, H. Ali | Yamali, Cem | Belveren, Samet | Demir, Yeliz | Aydınoğlu, Sabriye | Döndaş, Naciye Yaktubay | Taskin-Tok, Tugba | Taş, Senanur | Ülger, Mahmut | Sansano, Jose M. |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Acetylcholinesterase | Antimicrobial | Benzenesulfonamide | Carbonic anhydrase | Molecular docking | Pyrazole | Pyrrolidines |
Fecha de publicación: | 26-may-2023 |
Editor: | Taylor & Francis |
Cita bibliográfica: | Journal of Biomolecular Structure and Dynamics. 2023. https://doi.org/10.1080/07391102.2023.2214224 |
Resumen: | The synthesis and biological assessment of novel multi-functionalized pyrrolidine-containing benzenesulfonamides were reported along with their antimicrobial, antifungal, CAs inhibition, and AChE inhibition as well as DNA-binding effects. The chemical structure of the compounds was elucidated by using FTIR, NMR, and HRMS. Compound 3b, which had Ki values of 17.61 ± 3.58 nM (hCA I) and 5.14 ± 0.61 nM (hCA II), was found the be the most potent CAs inhibitor. Compounds 6a and 6b showed remarkable AChE inhibition effects with Ki values 22.34 ± 4.53 nM and 27.21 ± 3.96 nM in comparison to tacrine. Compounds 6a–6c had moderate antituberculosis effect on M. tuberculosis with a MIC value of 15.62 μg/ml. Compounds had weaker antifungal and antibacterial activity in the range of MIC 500–62.5 μg/ml against standard bacterial and fungal strains. Besides these above, molecular docking studies were performed to examine and evaluate the interaction of the remarkable compounds (3b, 6a and 6b) against the current enzymes (CAs and AChE). Novel compounds gained interest in terms of enzyme inhibitory potencies. Therefore, the most potent enzyme inhibitors may be considered lead compounds to be modified for further research. |
Patrocinador/es: | We gratefully acknowledge financial support from Çukurova University (Projects No: TSA-2021-13814 and TSA-2021-13443). |
URI: | http://hdl.handle.net/10045/140467 |
ISSN: | 0739-1102 (Print) | 1538-0254 (Online) |
DOI: | 10.1080/07391102.2023.2214224 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2023 Informa UK Limited, trading as Taylor & Francis Group |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1080/07391102.2023.2214224 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
---|---|---|---|---|
Poyraz_etal_2023_JBiomolStructDynam_final.pdf | Versión final (acceso restringido) | 4,09 MB | Adobe PDF | Abrir Solicitar una copia |
Todos los documentos en RUA están protegidos por derechos de autor. Algunos derechos reservados.