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

A wide range of 3-selenylindoles were synthesized via an eco-friendly approach that uses Oxone (R) 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. An eco-friendly approach that uses Oxone as the oxidant and iodine as the catalyst generates 3-selenelylindoles. Novel derivatives containing a benzenesulfonamide moiety were tested as human carbonic anhydrase I, II, IX and XII inhibitors.