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Publikācija: 5-Substituted-Benzylsulfanyl-Thiophene-2-Sulfonamides with Effective Carbonic Anhydrase Inhibitory Activity: Solution and Crystallographic Investigations

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language 5-Substituted-Benzylsulfanyl-Thiophene-2-Sulfonamides with Effective Carbonic Anhydrase Inhibitory Activity: Solution and Crystallographic Investigations
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Jekaterīna Ivanova
Agnese Balode
Raivis Žalubovskis
Janis Leitans
Andris Kazaks
Daniela Vullo
Kaspars Tārs
Claudiu T. Supuran
Keywords Carbonic anhydrase | Inhibitor | Mercaptan | Thiophene-2-sulfonamide
Abstract A series of 5-substituted-benzylsulfanyl-thiophene-2-sulfonamides was prepared by reacting 5-bromo-thiophene-2-sulfonamide with 5-substituted-benzyl mercaptans. The new compounds were investigated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The cytosolic human (h) isoforms hCA I was poorly inhibited by the new sulfonamides (KIs in the range of 683-4250nM), whereas hCA II, and the transmembrane, tumor associated isoforms hCA IX and XII were effectively inhibited in the subnanomolar-nanomolar range. A high resolution X-ray crystal structure of the adduct of hCA II with one of the new sulfonamides allowed us to rationalize the excellent inhibitory activity of these heterocyclic sulfonamides.
DOI: 10.1016/j.bmc.2016.11.045
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0968089616311166 
Reference Ivanova, J., Balode, A., Žalubovskis, R., Leitans, J., Kazaks, A., Vullo, D., Tārs, K., Supuran, C. 5-Substituted-Benzylsulfanyl-Thiophene-2-Sulfonamides with Effective Carbonic Anhydrase Inhibitory Activity: Solution and Crystallographic Investigations. Bioorganic and Medicinal Chemistry, 2017, Vol.25, Iss.3, pp.857-863. ISSN 0968-0896. Available from: doi:10.1016/j.bmc.2016.11.045
Additional information Citation count:
ID 24048