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Synthesis and Characterization of Novel 1,3-Diaryltriazene-Substituted Sulfaguanidine Derivatives as Selective Carbonic Anhydrase Inhibitors: Biological Evaluation, in Silico ADME/T and Molecular Docking Study.
- Source :
-
Chemistry & biodiversity [Chem Biodivers] 2023 Aug; Vol. 20 (8), pp. e202300611. Date of Electronic Publication: 2023 Aug 04. - Publication Year :
- 2023
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Abstract
- Sulfonamide compounds known as human carbonic anhydrase (hCA) inhibitors are used in the treatment of many diseases such as epilepsy, antibacterial, glaucoma, various diseases. 1,3-diaryl-substituted triazenes and sulfaguanidine are used for therapeutic purposes in many drug structures. Based on these two groups, the synthesis of new compounds is important. In the present study, the novel 1,3-diaryltriazene-substituted sulfaguanidine derivatives (SG1-13) were synthesized and fully characterized by spectroscopic and analytic methods. Inhibitory effect of these compounds on the hCA I and hCA II was screened as in vitro. All the series of synthesized compounds have been identified as potential hCA isoenzymes inhibitory with K <subscript>I</subscript> values in the range of 6.44±0.74-86.85±7.01 nM for hCA I and with K <subscript>I</subscript> values in the range of 8.16±0.40-77.29±9.56 nM for hCA II. Moreover, the new series of compounds showed a more effective inhibition effect than the acetazolamide used as a reference. The possible binding positions of the compounds with a binding affinity to the hCA I and hCA II was demonstrated by in silico studies. In conclusion, compounds with varying degrees of affinity for hCA isoenzymes have been designed and as selective hCA inhibitors. These compounds may be potential alternative agents that can be used to treat or prevent diseases associated with glaucoma and hCA inhibition.<br /> (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)
- Subjects :
- Humans
Carbonic Anhydrase Inhibitors pharmacology
Carbonic Anhydrase Inhibitors chemistry
Molecular Docking Simulation
Structure-Activity Relationship
Sulfaguanidine
Isoenzymes metabolism
Carbonic Anhydrase I metabolism
Molecular Structure
Carbonic Anhydrases metabolism
Glaucoma drug therapy
Subjects
Details
- Language :
- English
- ISSN :
- 1612-1880
- Volume :
- 20
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Chemistry & biodiversity
- Publication Type :
- Academic Journal
- Accession number :
- 37470688
- Full Text :
- https://doi.org/10.1002/cbdv.202300611