title: Synthesis of derivatives of the keto-pyrrolyl-difluorophenol scaffold: some structural aspects for aldose reductase inhibitory activity and selectivity.
abstract: Seven novel ARIs (3a-c, 4a-c and 5) were synthesized with the implementation of an optimized and, partially, selective synthetic procedure, via a Friedel-Crafts acylation reaction. The synthesized ARIs have values of IC(50)(ALR2) ranging from 0.19μM (in case of compound 3b) to 2.3μM (in case of compound 4a), while the values of selectivity index towards ALR1 range from 1 (in case of compound 3b) to 238 (in case of compound 3a). Finally, we found out that the presence of an additional (secondary) aromatic area is not a prerequisite feature for ARI activity.
authors: Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
authors: Eleni
authors: E
authors: Kotsampasakou
authors: Vassilis J
authors: VJ
authors: Demopoulos
mesh_terms: D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D005260:Female; D008297:Male; D019800:Phenol / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D011485:Protein Binding; D011758:Pyrroles / Q000737:chemistry*; D051381:Rats
chemical_list: D004791:Enzyme Inhibitors; D011758:Pyrroles; D019800:Phenol; D000449:Aldehyde Reductase