One pot synthesis of pyrrolidines type 3,7-diazabicyclo [3.3.0] octane and biological activity

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dc.contributor.authorAmornraksa, Kitti
dc.contributor.authorPrachayasittikul, Virapong
dc.contributor.authorWorachartcheewan, Apilak
dc.date.accessioned2008-12-05T12:49:38Z
dc.date.available2008-12-05T12:49:38Z
dc.date.issued2008-12-05T12:49:38Z
dc.description.abstractPyrrolidines 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.en
dc.identifier.issn1611-2156
dc.identifier.urihttp://hdl.handle.net/2003/25891
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-14396
dc.language.isoende
dc.relation.ispartofseriesEXCLI Journal ; Vol. 7, 2008en
dc.subject1-aminopyrrolidine-2,5-dioneen
dc.subjectantimicrobial and antioxidative activitiesen
dc.subjectpyrrolidineen
dc.subject.ddc610
dc.titleOne pot synthesis of pyrrolidines type 3,7-diazabicyclo [3.3.0] octane and biological activityen
dc.typeTextde
dc.type.publicationtypearticlede
dcterms.accessRightsopen access
eldorado.dnb.zdberstkatid2132560-1

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