Carbonic anhydrase inhibitors: synthesis of N-morpholylthiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV.
Several aromatic/heterocyclic sulfonamides possessing free amino, imino or hydrazino moieties were transformed into the corresponding N-morpholylthiocarbonylsulfenyl derivatives, by reaction with N-morpholyldithiocarbamate in the presence of oxidizing agents (NaClO or iodine). These compounds showed nanomolar inhibition against three CA isozymes, and interesting in vitro tumor cell growth inhibitory properties, against several leukemia, non-small cell lung, ovarian, melanoma, colon, CNS, renal, prostate and breast cancer cell lines.
Scozzafava
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Università degli Studi, Laborarorio di Chimica Inorganica e Bioinorganica, Florence, Italy.
Supuran
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D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000378:metabolism; D002455:Cell Division / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D009025:Morpholines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D014407:Tumor Cells, Cultured; D000096926:Benzenesulfonamides
D002257:Carbonic Anhydrase Inhibitors; D002256:Carbonic Anhydrases; D006571:Heterocyclic Compounds; D009025:Morpholines; D013449:Sulfonamides; C413741:4-((4-morpholinyl-thiocarbonylsulfenylamino)ethyl)benzenesulfonamide; D000096926:Benzenesulfonamides; C413740:4-((4-morpholinylthiocarbonylsulfenylamino)methyl)benzenesulfonamide