title: Organochalcogen compounds from glycerol: synthesis of new antioxidants.
abstract: We describe here a simple method for the synthesis of glycerol derivatives containing an organochalcogen unit (Se, Te and S) using NaBH4 and PEG-400 as a solvent. The new methodology was used to synthesize a range of new organochalcogen compounds in good yields. Furthermore, four of synthesized compounds were evaluated for their antioxidant activity using different assays, such as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, nitric oxide (NO) and hydroxyl radical (OH) scavenging, ferric ion reducing antioxidant power (FRAP), ferrous ion chelating, superoxide dismutase-like activity and inhibition of linoleic acid lipid peroxidation. The new organotellurium 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j showed antioxidant activity and was more effective in inhibition of induced lipid peroxidation compared to solketal 4. Selenium and sulfur analogs 3a and 3m and solketal 4 did not present antioxidant effect. These findings suggest that 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j is a promising antioxidant and that its activity is influenced by the presence of the tellurium atom on the structure.
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Patrick C
authors.initials: PC
authors.lastname: Nobre
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Elton L
authors.initials: EL
authors.lastname: Borges
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Cristian M
authors.initials: CM
authors.lastname: Silva
authors.affiliation: Grupo de Pesquisa em Neurobiotecnologia-GPN, CDTec, Unidade Biotecnologia, Universidade Federal de Pelotas, UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Angela M
authors.initials: AM
authors.lastname: Casaril
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil; Grupo de Pesquisa em Neurobiotecnologia-GPN, CDTec, Unidade Biotecnologia, Universidade Federal de Pelotas, UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Débora M
authors.initials: DM
authors.lastname: Martinez
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Eder J
authors.initials: EJ
authors.lastname: Lenardão
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil.
authors.forename: Diego
authors.initials: D
authors.lastname: Alves
authors.affiliation: Grupo de Pesquisa em Neurobiotecnologia-GPN, CDTec, Unidade Biotecnologia, Universidade Federal de Pelotas, UFPel, CEP 96010-900 Pelotas, RS, Brazil. Electronic address: luciellisavegnago@yahoo.com.br.
authors.forename: Lucielli
authors.initials: L
authors.lastname: Savegnago
authors.affiliation: Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas-UFPel, CEP 96010-900 Pelotas, RS, Brazil. Electronic address: gelson_perin@ufpel.edu.br.
authors.forename: Gelson
authors.initials: G
authors.lastname: Perin
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D018011:Chalcogens / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005990:Glycerol / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015227:Lipid Peroxidation / Q000187:drug effects; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D018011:Chalcogens; D016166:Free Radical Scavengers; D009942:Organometallic Compounds; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; D005990:Glycerol
keywords: Antioxidant activity; Glycerol derivatives; Organochalcogen compounds; PEG-400; Radical scavenging activity