Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-A rylidene-thiazolidine-2,4-dione Derivatives

Derivatives of the thiazolidine-2,4-dione core represent a heterocyclic class with several correlated properties. In this context, the synthesis of structural analogues of these bioactive substances becomes attractive in the field of medicinal chemistry. These analogues act as antimicrobial agents a...

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Published inJournal of the Brazilian Chemical Society Vol. 30; no. 1; pp. 164 - 172
Main Authors de Paiva, Raissa K. C., da Silva, Jamerson F., Moreira, Hudieyllen A., Pinto, Osvaldo G., Camargo, Lilian T. F. M., Naves, Plinio L. F., Camargo, Ademir J., Ribeiro, Luciano, Ramos, Luciana M.
Format Journal Article
LanguageEnglish
Published SAO PAULO Soc Brasileira Quimica 01.01.2019
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SYSTEM
CHALCONE DERIVATIVES
5-arylidenethiazolidine-2, 4-diones
ANALOGS
ANTIBACTERIAL
quantum chemical descriptors
organocatalyst
INHIBITORS
structure-activity relationship
principal component analysis
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Summary:Derivatives of the thiazolidine-2,4-dione core represent a heterocyclic class with several correlated properties. In this context, the synthesis of structural analogues of these bioactive substances becomes attractive in the field of medicinal chemistry. These analogues act as antimicrobial agents against Gram-positives pathogens. The present work aimed to synthesize 10 different derivatives of 5-arylidene-thiazolidine-2,4-dione, employing urea as the catalyst in a solvent-free reaction medium, with yields that ranged from 45 to 99%. The compounds obtained were submitted to an antimicrobial assay against S. aureus ATCC 29213. Two compounds presented minimum inhibitory concentration of 62.5 and 32.5 mu g mL(-1) and minimum bactericidal concentration < 500 mu gL(-1) demonstrating their antibacterial potential. Principal component analysis was carried out to discriminate the compounds in active and inactive classes. Four geometric and electronic molecular descriptors were required to completely discriminate the compounds. The selected descriptors can guide us in designing new 5-arylidene-thiazolidine-2,4-dione derivatives with enhanced activity.
ISSN:0103-5053
1678-4790
DOI:10.21577/0103-5053.20180167