Synthesis and Antimicrobial Activity of a New Series of Thiazolidine-2,4-diones Carboxamide and Amino Acid Derivatives

Rakia Abd Alhameed; Zainab Almarhoon; Sarah I Bukhari; Ayman El-Faham; Beatriz G de la Torre; Fernando Albericio

doi:10.3390/molecules25010105

Synthesis and Antimicrobial Activity of a New Series of Thiazolidine-2,4-diones Carboxamide and Amino Acid Derivatives

Molecules. 2019 Dec 27;25(1):105. doi: 10.3390/molecules25010105.

Authors

Rakia Abd Alhameed¹, Zainab Almarhoon¹, Sarah I Bukhari², Ayman El-Faham^{1

3}, Beatriz G de la Torre^{4

5}, Fernando Albericio^{1

5

6}

Affiliations

¹ Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
² Department of Pharmaceutics, College of Pharmacy, King Saud University, P.O. Box 4584, Riyadh 11451, Saudi Arabia.
³ Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 12321, Egypt.
⁴ KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South Africa.
⁵ Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa.
⁶ CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, and Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Spain.

Abstract

Novel thiazolidine-2,4-dione carboxamide and amino acid derivatives were synthesized in excellent yield using OxymaPure/N,N'-diisopropylcarbodimide coupling methodology and were characterized by chromatographic and spectrometric methods, and elemental analysis. The antimicrobial and antifungal activity of these derivatives was evaluated against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two-Gram negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and one fungal isolate (Candida albicans). Interestingly, several samples demonstrated weak to moderate antibacterial activity against Gram-negative bacteria, as well as antifungal activity. However, only one compound namely, 2-(5-(3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetic acid, showed antibacterial activity against Gram-positive bacteria, particularly S. aureus.

Keywords: OxymaPure; antibacterial activity; thiazolidine-2,4-dione amino acid ester; thiazolidine-2,4-dione carboxamide.

MeSH terms

Anti-Infective Agents* / chemical synthesis
Anti-Infective Agents* / chemistry
Anti-Infective Agents* / pharmacology
Bacteria / growth & development*
Candida albicans / growth & development*
Thiazolidinediones* / chemical synthesis
Thiazolidinediones* / chemistry
Thiazolidinediones* / pharmacology

Substances

Anti-Infective Agents
Thiazolidinediones

Abstract

MeSH terms

Substances

Grants and funding