Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities. (19th March 2020)

• Record Type: Journal Article
• Authors: Carrasco, Fernando; Hernández, Wilfredo; Chupayo, Oscar; Álvarez, Celedonio M.; Oramas-Royo, Sandra; Spodine, Evgenia; Tamariz-Angeles, Carmen; Olivera-Gonzales, Percy; Dávalos, Juan Z.
• Other Names: Navarrete-Vazquez Gabriel Academic Editor.
• Is Part Of: Journal of chemistry. Volume 2020(2020)
• Publication Date: 2020-03-19
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1155/2020/7157281
• Languages: English
• ISSNs: 2090-9063

Abstract

Abstract : 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, 1 H NMR, and 13 C 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 μ g/mL, respectively) and Bacillus subtilis (MIC = 100 and 150 μ g/mL, respectively). On the other hand, 3 and 4 were relatively less active against the tested bacterial strains compared with 1, 2, and tetracycline.