Imine derivatives were obtained by condensation of sulfanilamide with substituted aromatic aldehydes. The Schiff bases were thereafter reduced with sodium borohydride, leading to the corresponding amines, derivatives of 4-sulfamoylphenyl-benzylamine. These sulfonamides were investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). We noted that the compounds incorporating secondary amine moieties showed a better inhibitory activity against all CA isozymes compared to the corresponding Schiff bases. Low nanomolar CA II, IX and XII inhibitors were detected, whereas the activity against hCA I was less potent. The secondary amines incorporating sulfonamide or similar zinc-binding groups, poorly investigated chemotypes for designing metalloenzyme inhibitors, may offer interesting opportunities in the field due to the facile preparation and possibility to explore a vast chemical space.

通过磺胺与取代的芳族醛缩合获得亚胺衍生物。然后用硼氢化钠还原席夫碱，得到相应的胺，即4-氨磺酰基苯基-苄胺的衍生物。研究了这些磺酰胺作为人碳酸酐酶（hCA，EC 4.2.1.1）同工型hCA I和II（胞质同工酶）以及hCA IX和XII（跨膜，肿瘤相关酶）的抑制剂。我们注意到，与相应的席夫碱相比，掺有仲胺部分的化合物对所有CA同工酶表现出更好的抑制活性。检测到低纳摩尔CA II，IX和XII抑制剂，而针对hCA I的活性较低。结合了磺酰胺或类似锌结合基团的仲胺，