TY - JOUR
T1 - Organochalcogen compounds from glycerol
T2 - Synthesis of new antioxidants
AU - Nobre, Patrick C.
AU - Borges, Elton L.
AU - Silva, Cristian M.
AU - Casaril, Angela M.
AU - Martinez, Débora M.
AU - Lenardão, Eder J.
AU - Alves, Diego
AU - Savegnago, Lucielli
AU - Perin, Gelson
N1 - Funding Information:
The authors are grateful to FAPERGS and CNPq ( PRONEX 10/0005-1 , PRONEM 11/2026-4 ), CAPES and FINEP for the financial support.
Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.
PY - 2014/11/1
Y1 - 2014/11/1
N2 - 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 3j 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 3j is a promising antioxidant and that its activity is influenced by the presence of the tellurium atom on the structure.
AB - 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 3j 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 3j is a promising antioxidant and that its activity is influenced by the presence of the tellurium atom on the structure.
KW - Antioxidant activity
KW - Glycerol derivatives
KW - Organochalcogen compounds
KW - PEG-400
KW - Radical scavenging activity
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U2 - 10.1016/j.bmc.2014.08.018
DO - 10.1016/j.bmc.2014.08.018
M3 - Article
C2 - 25217848
AN - SCOPUS:84908440130
SN - 0968-0896
VL - 22
SP - 6242
EP - 6249
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 21
ER -