Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities

• Autores: Carrasco Solís, Fernando Carlos, Hernández Gorritti, Wilfredo Román, Chupayo, Oscar, Celedonio M., Álvarez, Oramas Royo, Sandra, Spodine, Evgenia, Tamariz Angeles, Carmen, Olivera Gonzale, Percy, Dávalos, Juan Z.
• Formato: artículo
• Fecha de Publicación: 2020
• Institución: Universidad de Lima
• Repositorio: ULIMA-Institucional
• Lenguaje: inglés
• OAI Identifier: oai:repositorio.ulima.edu.pe:20.500.12724/10791
• Enlace del recurso: https://hdl.handle.net/20.500.12724/10791; https://doi.org/10.1155/2020/7157281
• Nivel de acceso: acceso abierto
• Materia: Chemistry, Organic; Organic compounds; Química orgánica; Compuestos orgánicos; https://purl.org/pe-repo/ocde/ford#1.00.00

Four indole-3-carbaldehyde semicarbazone derivatives, 2-((5-bromo-1H-indol-3-yl)methylene)hydrazinecarboxamide (1), 2-((5-chloro-1H-indol-3-yl)methylene)hydrazinecarboxamide (2), 2-((5-methoxy-1H-indol-3-yl)methylene)hydrazinecarboxamide (3), and 2-((4-nitro-1H-indol-3-yl)methylene)hydrazinecarboxamide (4) were synthesized and characterized by ESI-MS and spectroscopic (FT-IR, 1H NMR, and 13C NMR) techniques. The two-dimensional NMR (in acetone-d6) spectral data revealed that the molecules 1 and 2 in solution are in the cisE isomeric form. This evidence is supported by DFT calculations at the B3LYP/6-311++G(d,p) level of theory where it was shown that the corresponding most stable conformers of the synthesized compounds have a cisE geometrical configuration, in both the gas and liquid (acetone and DMSO) phases. The in vitro antibacterial activity of compounds 1–4 was determined against Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Pseudomonas aeruginosa and Escherichia coli) bacteria. Among all the tested semicarbazones, 1 and 2 exhibited similar inhibitory activities against Staphylococcus aureus (MIC¿=¿100 and 150¿µg/mL, respectively) and Bacillus subtilis (MIC¿=¿100 and 150¿µg/mL, respectively). On the other hand, 3 and 4 were relatively less active against the tested bacterial strains compared with 1, 2, and tetracycline.