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Synthesis and Enzyme Inhibitory Activity of Novel Pyridine-2,6-dicarboxamides Bearing Primary Sulfonamide Groups

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Abstract

New pyridine-2,6-dicarboxamide derivatives containing sulfonamide groups were synthesized by the coupling of pyridine-2,6-dicarbonyl dichloride and various aminobenzenesulfonamides in a mixture of dichloromethane and acetone. The pyridinedicarboxamide-based sulfonamides were evaluated as carbonic anhydrase (CA) and cholinesterase (ChE) inhibitors, and they showed IC50 values in the ranges 12.8–37.6 nM against human carbonic anhydrase I (hCA I), 17.8–46.7 nM against human carbonic anhydrase II (hCA II), 98.4–197.5 nM against acetylcholinesterase (AChE), and 82.2–172.7 nM against butyrylcholinesterase (BuChE). These results are comparable with those for known inhibitors such as acetazolamide (IC50 = 32.1 nM for hCA I and IC50 = 51.0 nM for hCA II) and rivastigmine (IC50 = 60.2 nM for AChE and IC50 = 14.0 nM for BuChE), which qualifies the synthesized compounds as candidates for a more in-depth study.

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Acknowledgments

The authors thank Agri Ibrahim Cecen University for providing facilities for carrying out this research and Prof. R. Hunter for reviewing the manuscript.

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  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Agri Ibrahim Cecen University, Agri, Turkey

    N. Stellenboom & A. R. Baykan

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  1. N. Stellenboom
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  2. A. R. Baykan
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Correspondence to N. Stellenboom.

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Stellenboom, N., Baykan, A.R. Synthesis and Enzyme Inhibitory Activity of Novel Pyridine-2,6-dicarboxamides Bearing Primary Sulfonamide Groups. Russ J Org Chem 55, 1951–1956 (2019). https://doi.org/10.1134/S1070428019120248

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  • DOI: https://doi.org/10.1134/S1070428019120248

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