7-Chloroquinoline-1,2,3-triazoyl Carboxylates: Organocatalytic Synthesis and Antioxidant Properties

We describe herein our results on the synthesis and antioxidant properties of 7-chloroquinoline-1,2,3-triazoyl-4-carboxylates. This class of compounds have been synthesized in moderated to excellent yields by the reaction of 4-azido-7-chloroquinoline with a range of β-ketoesters in the presence of a...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2016-01, Vol.27 (1), p.41-53
Main Authors: Saraiva, Maiara T., Krüger, Roberta, Baldinotti, Rodolfo S. M., Lenardão, Eder J., Luchese, Cristiane, Savegnago, Lucielli, Wilhelm, Ethel A., Alves, Diego
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:We describe herein our results on the synthesis and antioxidant properties of 7-chloroquinoline-1,2,3-triazoyl-4-carboxylates. This class of compounds have been synthesized in moderated to excellent yields by the reaction of 4-azido-7-chloroquinoline with a range of β-ketoesters in the presence of a catalytic amount of pyrrolidine (10 mol%). The synthesized compounds ethyl 1-(7-chloroquinolin-4-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylate and ethyl 1-(7-chloroquinolin-4-yl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate were screened for their in vitro antioxidant activity and the results demonstrated that the first compound reduces the lipid peroxidation levels induced by sodium nitroprusside in liver of mice, while the second compound shown nitric oxide scavenging activity. This is an efficient method to produce new heterocyclic compounds with potential antioxidant activities.
ISSN:0103-5053
1678-4790
DOI:10.5935/0103-5053.20150239