Synthesis and evaluation of anti- Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles

• Published in: European journal of medicinal chemistry 2010-09, Vol.45 (9), p.3685-3691
• Main Authors: Liesen, André P., de Aquino, Thiago M., Carvalho, Cristiane S., Lima, Vânia T., de Araújo, Janete M., de Lima, José G., de Faria, Antônio R., de Melo, Edésio J.T., Alves, Antonio J., Alves, Elias W., Alves, Anselmo Q., Góes, Alexandre J.S.
• Format: Article
• Language: English
• Subjects: 1,3,4-Thiadiazole; 4-Thiazolidinone; Animals; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antimicrobial activity; Antiparasitic agents; Antiprotozoal Agents - chemical synthesis; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - pharmacology; Bacteria - drug effects; Biological and medical sciences; Cercopithecus aethiops; Drug Resistance; Fungi - drug effects; General aspects; Imidazole; Intracellular Space - drug effects; Intracellular Space - parasitology; Medical sciences; Microbial Sensitivity Tests; Pharmacology. Drug treatments; Semicarbazides - chemical synthesis; Semicarbazides - chemistry; Semicarbazides - pharmacology; Thiazolidines - chemical synthesis; Thiazolidines - chemistry; Thiazolidines - pharmacology; Toxoplasma - drug effects; Toxoplasma - physiology; Toxoplasma gondii; Vero Cells
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.05.017

In this work we reported the synthesis and evaluation of anti- Toxoplasma gondii and antimicrobial activities in vitro of three new compound series obtained from ethyl(5-methyl-1- H-imidazole-4-carboxylate): acylthiosemicarbazide analogues 3a– d, 4-thiazolidinone analogues 4a– d and 1,3,4-thiadiazole analogues 5a– d. All synthesized compounds were characterized by IR, 1H, 13C NMR and HRMS. The majority of the tested compounds show excellent anti- T. gondii activity when compared to hydroxyurea and sulfadiazine. In addition it was also shown that most of the compounds in this study have a better performance against intracellular tachyzoites. The results for antimicrobial activity evaluation showed weak antibacterial and antifungal activities for all the tested molecules, when compared with the standard drugs (chloramphenicol and rifampicin for antibacterial activity; nistatin and ketoconazole for antifungal activity). [Display omitted]