Synthesis, antioxidant and antichagasic properties of a selected series of hydroxy-3-arylcoumarins. Issue 2 (15th January 2017)

• Record Type: Journal Article
• Authors: Robledo-O'Ryan, Natalia; Matos, Maria João; Vazquez-Rodriguez, Saleta; Santana, Lourdes; Uriarte, Eugenio; Moncada-Basualto, Mauricio; Mura, Francisco; Lapier, Michel; Maya, Juan Diego; Olea-Azar, Claudio
• Is Part Of: Bioorganic & medicinal chemistry. Volume 25:Issue 2(2017)
• Page Start: 621
• Page End: 632
• Publication Date: 2017-01-15
• Subjects: Hydroxy-3-arylcoumarins -- Antioxidant activity -- Trypanosome -- Chagas disease; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.11.033
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: Oxidative stress is involved in several parasitic diseases such as Chagas. Agents able to selectively modulate biochemical processes involved in the disease represent promising multifunctional agents for the delay or abolishment of the progression of this pathology. In the current work, differently substituted hydroxy-3-arylcoumarins are described, exerting both antioxidant and trypanocidal activity. Among the compounds synthesized, compound8 showed the most interesting profile, presenting a moderate scavenging ability for peroxyl radicals (ORAC-FL = 2.23) and a high degree of selectivity towards epimastigotes stage of the parasite T. cruzi (IC50 = 1.31 μM), higher than Nifurtimox (drug currently used for treatment of Chagas disease). Interestingly, the current study revealed that small structural changes in the hydroxy-3-arylcoumarin core allow modulating both activities, suggesting that this scaffold has desirable properties for the development of promising classes of antichagasic compounds.