Authors: | Amornraksa, Kitti Prachayasittikul, Virapong Worachartcheewan, Apilak |
Title: | One pot synthesis of pyrrolidines type 3,7-diazabicyclo [3.3.0] octane and biological activity |
Language (ISO): | en |
Abstract: | Pyrrolidines type 2,4-disubstituted (alkyl, aryl or heteroaryl)-6,8-dioxo-3,7-diazabicyclo [3.3.0] octanes (8a-d) were successfully synthesized by an efficient one pot 1,3-dipolar cycloaddition of azomethine ylides (in situ generated from the reaction of aromatic aldehydes and methyl ester of alpha-amino acids) with dipolarophile (N-phenylmaleimide). The reaction of compounds 8a-d with hydrazine in ethanol at room temperature took place under nucleophilic substitution which furnished 5-amino-4,6-dioxo-octahydropyrrolo [3,4-b] pyrrole-3-carboxylic acid phenylamides (12a-d). Structures of the products were confirmed by IR and 1H NMR. The compounds (8b and 12a) were evaluated for antimicrobial (agar dilution method) and antioxidative (DPPH; 2,2-diphenyl-1-picrylhydrazyl and SOD; superoxide dismutase assays) activities. The results showed that at concentrations of 4-256 µg/mL, the tested compounds exhibited non-significant antimicrobial growth, whereas the 12a at 200 µg/mL began to exert some antioxidative activity. |
Subject Headings: | 1-aminopyrrolidine-2,5-dione antimicrobial and antioxidative activities pyrrolidine |
URI: | http://hdl.handle.net/2003/25891 http://dx.doi.org/10.17877/DE290R-14396 |
Issue Date: | 2008-12-05T12:49:38Z |
Appears in Collections: | Original Articles |
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Prachayasittikul_041208_proof.pdf | DNB | 315.87 kB | Adobe PDF | View/Open |
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