Iodine/Oxone® oxidative system for the synthesis of selenylindoles bearing a benzenesulfonamide moiety as carbonic anhydrase I, II, IX, and XII inhibitors

Martina Palomba; Andrea Angeli; Riccardo Galdini; Alexandra Joana Hughineata; Gelson Perin; Eder João Lenardão; Francesca Marini; Claudio Santi; Claudiu T. Supuran; Luana Bagnoli

doi:10.1039/D4OB00826J

Iodine/Oxone® oxidative system for the synthesis of selenylindoles bearing a benzenesulfonamide moiety as carbonic anhydrase I, II, IX, and XII inhibitors†

Martina Palomba,‡^a Andrea Angeli,‡^b Riccardo Galdini,^a Alexandra Joana Hughineata,^a Gelson Perin,^c Eder João Lenardão,

^c Francesca Marini,

^a Claudio Santi,

*^a Claudiu T. Supuran

^b and Luana Bagnoli

*^a

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^a Department of Pharmaceutical Sciences (Group of Catalysis, Synthesis and Organic Green Chemistry), University of Perugia, Via del Liceo, 1-06123 Perugia, Italy
E-mail: luana.bagnoli@unipg.it, claudio.santi@unipg.it

^b University of Florence, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy

^c Laboratório de Síntese Orgânica Limpa (LASOL), Centro de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, CEP: 96010-900 Pelotas, RS, Brazil

Abstract

A wide range of 3-selenylindoles were synthesized via an eco-friendly approach that uses Oxone® as the oxidant in the presence of a catalytic amount of iodine. This mild and economical protocol showed broad functional group tolerance and operational simplicity. A series of novel selenylindoles bearing a benzenesulfonamide moiety were also synthesized and evaluated as carbonic anhydrase inhibitors of the human (h) isoforms hCa I, II, IX, and XII, which are involved in pathologies such as glaucoma and cancer. Several derivatives showed excellent inhibitory activity towards these isoforms in the nanomolar range, lower than that shown by acetazolamide.

Organic & Biomolecular Chemistry

Iodine/Oxone® oxidative system for the synthesis of selenylindoles bearing a benzenesulfonamide moiety as carbonic anhydrase I, II, IX, and XII inhibitors†

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Iodine/Oxone® oxidative system for the synthesis of selenylindoles bearing a benzenesulfonamide moiety as carbonic anhydrase I, II, IX, and XII inhibitors

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