碘/过氧单磺酸钾氧化体系在合成含苯磺酰胺部分的硒吲哚中的应用，作为碳酸酐酶 I、II、IX 和 XII 的抑制剂。
Iodine/Oxone® oxidative system for the synthesis of selenylindoles bearing a benzenesulfonamide moiety as carbonic anhydrase I, II, IX, and XII inhibitors.
机构信息
Department of Pharmaceutical Sciences (Group of Catalysis, Synthesis and Organic Green Chemistry), University of Perugia, Via del Liceo, 1-06123 Perugia, Italy.
University of Florence, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy.
出版信息
Org Biomol Chem. 2024 Aug 14;22(32):6532-6542. doi: 10.1039/d4ob00826j.
A wide range of 3-selenylindoles were synthesized 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.
采用一种绿色环保的方法，使用 Oxone®作为氧化剂，在催化量碘的存在下，合成了一系列 3-硒吲哚。该温和、经济的方法具有广泛的官能团容忍性和操作简单性。还合成了一系列新型的苯磺酰胺取代的硒吲哚，并将其作为碳酸酐酶抑制剂对人（h）同工型 hCa I、II、IX 和 XII 进行了评估，这些同工型与青光眼和癌症等疾病有关。一些衍生物对这些同工型具有优异的抑制活性，其纳摩尔范围低于乙酰唑胺。
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