A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase |
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| Institution: | 1. Institute of Chemistry, St. Petersburg State University, 199034 St. Petersburg, Russian Federation;2. Center for Bio- and Chemoinformatics, I. M. Sechenov First Moscow State Medical University, 119991 Moscow, Russian Federation;3. Department of Neurofarba, Universita degli Studi di Firenze, 50019 Florence, Italy;4. Immanuel Kant Baltic Federal University, 236041 Kaliningrad, Russian Federation;5. Pharmaceutical Technology Transfer Center, Yaroslavl State Pedagogical University named after K. D. Ushinsky, 150000 Yaroslavl, Russian Federation;1. A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. National Research University Higher School of Economics (HSE University), 101000 Moscow, Russian Federation;3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;4. G. V. Plekhanov Russian University of Economics, 117997 Moscow, Russian Federation;5. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;1. Institute of Macromolecular Compounds, Russian Academy of Sciences, 199004 St. Petersburg, Russian Federation;2. Saint-Petersburg State University of Industrial Technologies and Design, 191186 St. Petersburg, Russian Federation;3. St. Petersburg State Institute of Technology (Technical University), 190013 St. Petersburg, Russian Federation;4. Institute of Earth Sciences, St. Petersburg State University, 199034 St. Petersburg, Russian Federation;1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 119334 Moscow, Russian Federation;3. Photochemistry Centre, FRC ‘Crystallography and Photonics’, Russian Academy of Sciences, 119421 Moscow, Russian Federation |
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| Abstract: | An N,N-bis(p-methoxybenzyl)-protected α-acetyl-α-diazo-methane sulfonamide proved to be a useful building block for accessing new 5-methyl-1,2,3-thiadiazole-4-sulfonamide as well as methyl 3-sulfamoyl-1H-pyrazole-5-carboxylate. The latter was further subjected to N-alkylation and N-arylation reactions. All resulting compounds showed potent inhibition of I, II and particularly of cancer-related IX and XII isoforms of human carbonic anhydrase. |
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| Keywords: | α-acetyl-α-diazomethane sulfonamide methyl propiolate [3 + 2] dipolar cycloaddition Lawesson’ reagent Chan–Evans–Lam arylation pyrazoles 1 2 3-thiadiazoles |
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