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Design, synthesis, biological evaluation and docking analysis of pyrrolidine-benzenesulfonamides as carbonic anhydrase or acetylcholinesterase inhibitors and antimicrobial agents.

Authors
  • Poyraz, Samet1
  • Döndaş, H Ali1, 2
  • Yamali, Cem1
  • Belveren, Samet1
  • Demir, Yeliz3
  • Aydınoglu, Sabriye4
  • Döndaş, Naciye Yaktubay5
  • Taskin-Tok, Tugba6, 7
  • Taş, Senanur2
  • Ülger, Mahmut8
  • Sansano, Jose M9
  • 1 Department of Analytical Chemistry, Faculty of Pharmacy, Mersin University, Mersin, Türkiye.
  • 2 Department of Biotechnology, Institute of Natural and Applied Sciences, Çukurova University, Balcalı, Adana, Türkiye.
  • 3 Ardahan University, Department of Pharmacy Services, Nihat Delibalta Göle Vocational High School, Ardahan, Türkiye.
  • 4 Çukurova University, Faculty of Pharmacy, Department of Analytical Chemistry, Balcalı, Adana, Türkiye.
  • 5 Çukurova University, Faculty of Medicine, Department of Pharmacology, Balcalı, Adana, Türkiye.
  • 6 Department of Chemistry, Faculty of Arts and Sciences, Gaziantep University, Gaziantep, Türkiye.
  • 7 Department of Bioinformatics and Computational Biology, Institute of Health Sciences, Gaziantep University, Gaziantep, Türkiye.
  • 8 Mersin University, Faculty of Pharmacy, Department of Pharmaceutical Microbiology, Mersin, Türkiye.
  • 9 University of Alicante, Department of Organic Chemistry, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Instituto de Síntesis Orgánica (ISO), Alicante, Spain. , (Spain)
Type
Published Article
Journal
Journal of biomolecular structure & dynamics
Publication Date
May 26, 2023
Pages
1–18
Identifiers
DOI: 10.1080/07391102.2023.2214224
PMID: 37232497
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

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.Communicated by Ramaswamy H. Sarma.

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