A series of hitherto unknown sulfonamide-incorporated αaminophosphonate derivatives were synthesized through the one-pot, twostep FeCl 3 -catalyzed coupling of 4-aminobenzenesulfonamide with the appropriate benzaldehydes and diethyl phosphite. The new sulfonamides inhibition studies were performed on four carbonic anhydrase isoforms, i.e., the cytosolic human (h) hCA I and II (off-targets) as well as transmembrane cancer-related hCA IX and XII (targets). Among the synthesized compounds, derivative 23 resulted in the most selective compound against both cancer-associated isoforms over the off-target hCA I (hCA I/IX = 78; hCA I/XII = 458) and hCA II (hCA II/IX = 10; hCA II/XII = 56) and the binding mode of both enantiomers R and S was investigated in silico.
Structural analysis of a set of phosphoramide/thiophosphoramide derivatives by scrutinizing the energy and topological calculations discloses the role of individual interactions in crystal formation.
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