Cancer is the second most common cause of death in the world. One of the objectives of this thesis is to biologically evaluate a series of anti-cancer polymeric aromatic/heterocyclic bis-sulfonamides and pyridinium sulfonamides which were synthesized from three established aminosulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitor pharmacophores. Testing of these novel inhibitors and their precursors against a panel of membrane-bound CA isoforms, including tumor-overexpressed CA IX and XII and cytosolic isozymes, identified nanomolar-potent inhibitors against both classes and several compounds with medium isoform selectivity. In the case of pyridinium sulfonamides we used complexes of the inhibitors with cyclodextrins or sulfocalixarene to enhance aqueous solubility for biological testing. The ability of CA inhibitors to kill tumor cells overexpressing CA IX and XII was tested under normoxic and hypoxic conditions, using 2D and 3D in vitro cellular models. The study identified a nanomolar potent PEGylated bis-sulfonamide CA inhibitor (25), as well as cyclodextrin and sulfocalixarenes complexes, which were able to significantly reduce the viability of colon HT-29, breast MDA-MB231, and ovarian SKOV-3 cancer cell lines, thus revealing the potential of polymer conjugates in CA inhibition and cancer treatment. As a different disease state yet still a concern, cognitive dysfunction markedly impacts patients with a host of psychiatric conditions including attention deficit hyperactivity disorder, autism spectrum disorder, drug addiction, schizophrenia, depression, bipolar disorder, obsessive-compulsive disorder, and of course, Parkinson’s and Alzheimer’s diseases and other types of dementia. Another objective of this thesis was to profile several series of bis-imidazoles for physicochemical, in-vitro and in-vivo properties as potential memory and learning enhancers (nootropics). Biological testing on eight isozymes of carbonic anhydrase (CA) present in the human brain revealed compounds with nanomolar potency against at least one membrane bound, cytosolic or mitochondrial CA isozymes, combined with good physicochemical properties. We also identified lead compounds with the ability to rescue experimental animals from drug-induced memory deficits, using an optimized Novel Object Recognition Task (NORT) procedure. / Pharmaceutical Sciences