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

AuthorsCarrasco, F.; Hernández, W.; Chupayo, Oscar; Álvarez, Celedonio M.; Oramas-Royo, S.; Spodine, E.; Tamariz-Angeles, C.; Olivera-Gonzales, P.; Dávalos, J.Z.
Issue Date19-Mar-2020
PublisherHindawi Publishing Corporation
CitationJournal of Chemistry 2020: 7157281 (2020)
AbstractFour 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, H NMR, and C NMR) techniques. The two-dimensional NMR (in acetone-d) 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.
Description9 pags., 2 figs., 2 tabs.
Publisher version (URL)http://dx.doi.org/10.1155/2020/7157281
Identifiersdoi: 10.1155/2020/7157281
issn: 2090-9071
Appears in Collections:(IQFR) Artículos
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