title: Synthesis of photosynthesis-inhibiting nostoclide analogues.
abstract: A series of 34 3-benzyl-5-(arylmethylene)furan-2(5H)-ones, designed using the naturally occurring toxins nostoclides as a lead structure, was synthesized as potential inhibitors of the photosynthetic electron transport. All compounds were fully characterized by IR, NMR (1H and 13C), and MS spectrometry. HMBC and HSQC bidimensional experiments allowed 13C and 1H assignments. Their biological activities were evaluated in vitro as the ability to interfere with light-driven reduction of ferricyanide by isolated spinach chloroplasts. About two-thirds of the compounds exhibited inhibitory properties in the micromolar range against the basal electron flow from water to K3[Fe(CN)6]. The inhibitory potential of these 3-benzyl-5-(arylmethylene)furan-2(5H)-one lactones is higher than that of other nostoclide analogues previously synthesized in the same laboratories.
authors.affiliation: Department of Chemistry, Federal University of Viçosa, Viçosa, MG, Brazil.
authors.forename: Róbson R
authors.initials: RR
authors.lastname: Teixeira
authors.forename: Luiz C A
authors.initials: LC
authors.lastname: Barbosa
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Forlani
authors.forename: Dorila
authors.initials: D
authors.lastname: Piló-Veloso
authors.forename: José
authors.initials: J
authors.lastname: Walkimar de Mesquita Carneiro
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D004579:Electron Transport / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D010788:Photosynthesis / Q000187:drug effects*; D020524:Thylakoids / Q000378:metabolism
chemical_list: D015107:4-Butyrolactone