title: Synthesis and biological evaluation of (2,5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-ones as free radical scavengers.
abstract: The allylation of aminocoumarins in the presence of excess of anhydrous K(2)CO(3) and allyl bromide to diallylaminocoumarins is described. The Ring Closing Metathesis reaction of the later with the Grubbs' 1rst generation catalyst under reflux or MW irradiation has resulted mainly to (2,5-dihydro-1H-pyrrol-1-yl)coumarins and (1H-pyrrol-1-yl)coumarins. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase LO and (v) to scavenge hydroxyl radicals. Most of them were found to be potent lipid peroxidation inhibitors in vitro. The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 11a and 12c presenting higher LO inhibitory activity as well as compound 17 were found to present a promising antioxidant and LO inhibitory profile.
authors: Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece.
authors: Anna
authors: A
authors: Balabani
authors: Dimitra J
authors: DJ
authors: Hadjipavlou-Litina
authors: Konstantinos E
authors: KE
authors: Litinas
authors: Maria
authors: M
authors: Mainou
authors: Crystal-Catherine
authors: CC
authors: Tsironi
authors: Anastasia
authors: A
authors: Vronteli
mesh_terms: D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D017665:Hydroxyl Radical / Q000037:antagonists & inhibitors / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013025:Glycine max / Q000201:enzymology
chemical_list: D003374:Coumarins; D016166:Free Radical Scavengers; D016859:Lipoxygenase Inhibitors; D017665:Hydroxyl Radical; D008084:Lipoxygenase