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Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors.
Bioorg Med Chem Lett. 2014 Aug 01; 24(15):3422-5.BM

Abstract

A series of secondary and tertiary aryl sulfonamides were synthesized under flow conditions and evaluated for their ability to selectively inhibit tumor-associated carbonic anhydrase isoforms IX and XII. The tested compounds revealed to be highly potent CA IX inhibitors in nanomolar range, and to inhibit CA XII activity with different ranks of potencies. Remarkably, 4-methyl-N-phenyl-benzenesulfonamide was a selective nanomolar CA IX inhibitor with an IC50 of 90 nM.

Authors+Show Affiliations

Laboratory of Medicinal and Advanced Synthetic Chemistry (Lab MASC), Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, Perugia I-06123, Italy.Laboratory of Medicinal and Advanced Synthetic Chemistry (Lab MASC), Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, Perugia I-06123, Italy.Laboratory of Bioinorganic Chemistry, University of Florence, Via della Lastruccia 3, Sesto Fiorentino (Firenze) I-50019, Italy.Neurofarba Dept., Section of Pharmaceutical and Nutriceutical Sciences, University of Florence, Via U. Schiff 6, Sesto Fiorentino (Firenze) I-50019, Italy.Laboratory of Medicinal and Advanced Synthetic Chemistry (Lab MASC), Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, Perugia I-06123, Italy. Electronic address: antimo.gioiello@unipg.it.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24948563

Citation

Rosatelli, Emiliano, et al. "Flow Synthesis and Biological Activity of Aryl Sulfonamides as Selective Carbonic Anhydrase IX and XII Inhibitors." Bioorganic & Medicinal Chemistry Letters, vol. 24, no. 15, 2014, pp. 3422-5.
Rosatelli E, Carotti A, Ceruso M, et al. Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors. Bioorg Med Chem Lett. 2014;24(15):3422-5.
Rosatelli, E., Carotti, A., Ceruso, M., Supuran, C. T., & Gioiello, A. (2014). Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors. Bioorganic & Medicinal Chemistry Letters, 24(15), 3422-5. https://doi.org/10.1016/j.bmcl.2014.05.086
Rosatelli E, et al. Flow Synthesis and Biological Activity of Aryl Sulfonamides as Selective Carbonic Anhydrase IX and XII Inhibitors. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3422-5. PubMed PMID: 24948563.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors. AU - Rosatelli,Emiliano, AU - Carotti,Andrea, AU - Ceruso,Mariangela, AU - Supuran,Claudiu T, AU - Gioiello,Antimo, Y1 - 2014/06/04/ PY - 2014/03/21/received PY - 2014/05/21/revised PY - 2014/05/22/accepted PY - 2014/6/21/entrez PY - 2014/6/21/pubmed PY - 2015/3/7/medline KW - Carbonic anhydrases KW - Docking KW - Flow synthesis KW - Sulfonamides SP - 3422 EP - 5 JF - Bioorganic & medicinal chemistry letters JO - Bioorg. Med. Chem. Lett. VL - 24 IS - 15 N2 - A series of secondary and tertiary aryl sulfonamides were synthesized under flow conditions and evaluated for their ability to selectively inhibit tumor-associated carbonic anhydrase isoforms IX and XII. The tested compounds revealed to be highly potent CA IX inhibitors in nanomolar range, and to inhibit CA XII activity with different ranks of potencies. Remarkably, 4-methyl-N-phenyl-benzenesulfonamide was a selective nanomolar CA IX inhibitor with an IC50 of 90 nM. SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/24948563/Flow_synthesis_and_biological_activity_of_aryl_sulfonamides_as_selective_carbonic_anhydrase_IX_and_XII_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(14)00595-2 DB - PRIME DP - Unbound Medicine ER -