The aim of this study was to identify inhibition of carbonic anhydrase I and II (CA I and II) isozymes by azido sulfonyl carbamates through both and approaches and also to determine the drug-likeness properties and antibacterial activities of azido sulfonyl carbamates. inhibition and molecular docking studies of azido sulfonyl carbamate derivatives () on isozymes were performed. Except for derivative , all derivatives inhibited human CA I and II. Almost all compounds had antibacterial effects. The docking results showed that compound had the best results, with binding energy of -8.20 kcal/mol for human CA I and -8.24 kcal/mol for human CA II. Molecule inhibited only CA I. Its usage as a potential chemotherapeutic agent specific to the CA I isozyme may be considered.
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http://dx.doi.org/10.4155/fmc-2020-0387 | DOI Listing |
Beilstein J Org Chem
March 2024
Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia.
2-Chloro-4-sulfonylquinazolines undergo functional group swap when treated with an azide nucleophile: 1) the azide replaces the sulfonyl group at the C4 position; 2) the intrinsic azide-tetrazole tautomeric equilibrium directs the nucleofugal sulfinate from the first step to replace chloride at the C2 position. This transformation is effective with quinazolines bearing electron-rich substituents. Therefore, the title transformations are demonstrated on the 6,7-dimethoxyquinazoline core, which is present in pharmaceutically active substances.
View Article and Find Full Text PDFCarbohydr Res
February 2024
Department of Chemistry, University of Alberta, Edmonton Alberta, T6G 2G2, Canada. Electronic address:
Neuraminic acid (Neu5Ac, also known as sialic acid) is an important monosaccharide found in glycoproteins and glycolipids which plays a vital role in regulation of physiological functions and pathological conditions. The study of sialoglycans has benefitted from the development of glycomimetic probes and inhibitors for proteins and enzymes that interact with and modify neuraminic acid in glycan chains. Methods to access sialoside intermediates with high yield are needed to facilitate the design of new targets.
View Article and Find Full Text PDFEnzyme Microb Technol
August 2023
Division of Organic Chemistry & Biochemistry, Ruđer Bošković Institute, Zagreb, Croatia.
Within the last decade, the field of bio-nanoengineering has achieved significant advances allowing us to generate, e.g., nanoscaled molecular machineries with arbitrary shapes.
View Article and Find Full Text PDFMolecules
October 2022
Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, Peterhof 198504, Russia.
Based on the previously reported involvement of homophthalic acid monoesters in the Castagnoli-Cushman reaction-type cyclocondensation with imines, we tested a number of other -methyl benzoic acids bearing various electron-withdrawing groups in the α-position. The majority of these substrates delivered the expected tetrahydroisoquinolone adducts on activation with CDI or acetic anhydride. Homophthalic acid mononitriles displayed the highest promise as substrates for the new reaction, both in terms of scope and product yields.
View Article and Find Full Text PDFOrg Lett
October 2022
Graduate School of Pharmaceutical Sciences, Nagoya University, Nagoya 464-8601, Japan.
Upon treatment of α-azido sulfones with a thiol in the presence of 1,1,3,3-tetramethylguanidine, substitution of the sulfonyl group with a thiolate occurred, resulting in the formation of α-azido sulfides. Based on experimental results and DFT calculations, a reaction mechanism that involves the addition of a thiolate to the azido group and generation of an alkylidene triazene is proposed.
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