Contribution to the Synthesis, Characterization, Separation and Quantification of New N-Acyl Thiourea Derivatives with Antimicrobial and Antioxidant Potential

Author:

Roman Roxana1,Pintilie Lucia2ORCID,Nuță Diana Camelia1ORCID,Căproiu Miron Teodor3,Dumitrașcu Florea3,Zarafu Irina4ORCID,Ioniță Petre4ORCID,Marinaș Ioana Cristina56ORCID,Măruțescu Luminița67,Kapronczai Eleonora8ORCID,Ardelean Simona9,Limban Carmen1

Affiliation:

1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania

2. National Institute of Chemical-Pharmaceutical Research & Development, 112 Vitan Av., 031299 Bucharest, Romania

3. “C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independenței, 060023 Bucharest, Romania

4. Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, Romania

5. Research Institute of the University of Bucharest, University of Bucharest, 90 Panduri Road, 030018 Bucharest, Romania

6. Sanimed International Impex S.R.L., 087040 Calugareni, Romania

7. Department of Microbiology and Immunology, Faculty of Biology, University of Bucharest, 91-96 Splaiul Independenței, 060101 Bucharest, Romania

8. Supramolecular Organic and Organometallic Chemistry Centre, Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany János, 400028 Cluj-Napoca, Romania

9. Department of Pharmaceutical Technology, Faculty of Pharmacy, “Vasile Goldiș” Western University, 86 Liviu Rebreanu, 310045 Arad, Romania

Abstract

The present study aimed to synthesize, characterize, and validate a separation and quantification method of new N-acyl thiourea derivatives (1a–1o), incorporating thiazole or pyridine nucleus in the same molecule and showing antimicrobial potential previously predicted in silico. The compounds have been physiochemically characterized by their melting points, IR, NMR and MS spectra. Among the tested compounds, 1a, 1g, 1h, and 1o were the most active against planktonic Staphylococcus aureus and Pseudomonas aeruginosa, as revealed by the minimal inhibitory concentration values, while 1e exhibited the best anti-biofilm activity against Escherichia coli (showing the lowest value of minimal inhibitory concentration of biofilm development). The total antioxidant activity (TAC) assessed by the DPPH method, evidenced the highest values for the compound 1i, followed by 1a. A routine quality control method for the separation of highly related compounds bearing a chlorine atom on the molecular backbone (1g, 1h, 1i, 1j, 1m, 1n) has been developed and validated by reversed-phase high-performance liquid chromatography (RP—HPLC), the results being satisfactory for all validation parameters recommended by the ICH guidelines (i.e., system suitability, specificity, the limits of detection and quantification, linearity, precision, accuracy and robustness) and recommending it for routine separation of these highly similar compounds.

Funder

University of Medicine and Pharmacy Carol Davila

“Carol Davila” University of Medicine and Pharmacy Bucharest

Publisher

MDPI AG

Subject

Pharmaceutical Science

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