New Semisynthetic Penicillins Obtained by Coupling of the 6-Aminopenicillanic Acid with 5-Mercapto-1,2,4-triazoles-3,4-disubstituted

• Published in: International journal of molecular sciences 2023-01, Vol.24 (2), p.1497
• Main Authors: Cheptea, Corina, Zara, Alexandru, Dimitriu, Dan Gheorghe, Sunel, Valeriu, Dorohoi, Dana Ortansa, Cigu, Toni Andor
• Format: Article
• Language: English
• Subjects: Acids; Acylation; Amides; Aminopenicillanic acid; Amoxicillin; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibiotics; Antifungal agents; Antimicrobial agents; Penicillanic acid derivatives; Penicillin; Penicillins - pharmacology; Sodium; Sodium salts; Spectroscopy, Fourier Transform Infrared; Sulfur; Triazoles; Triazoles - chemistry; Triazoles - pharmacology; β-Lactam antibiotics
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms24021497

In a basic medium, 5-Mercapto-1,2,4-triazoles pass into the thiol form, allowing their transformation into sodium salts, which, in reaction with sodium monochloroacetate, lead to sodium 5-thioacetates of 1,2,4-triazoles-3,4-disubstituted. Sulfur derivatives converted to pivalic mixed anhydrides were used as active forms in the acylation of 6-amino penicillanic acid (6-AP) to obtain new semisynthetic penicillins. They contain in the molecule, together with the β-lactam ring, the nucleus 3-[(5-nitroindazol-1'-yl-methyl)]-4-aryl-5-mercapto-1,2,4-triazole, both contributing to an important antibacterial effect. The structure of the new antibiotics was confirmed by the results of elemental and spectral analysis (FT-IR, H- and C-NMR). The synthetic penicillins were tested for toxicological action and antibacterial activity and the obtained results were close to those for amoxicillin, the reference drug.