Indole-3-carbaldehyde semicarbazone derivatives: synthesis, characterization, and antibacterial activities
Author
dc.contributor.author
Carrasco, Fernando
Author
dc.contributor.author
Hernández, Wilfredo
Author
dc.contributor.author
Chupayo, Óscar
Author
dc.contributor.author
Álvarez, Celedonio M.
Author
dc.contributor.author
Oramas Royo, Sandra
Author
dc.contributor.author
Spodine Spiridonova, Evgenia
Author
dc.contributor.author
Tamariz-Ángeles, Carmen
Author
dc.contributor.author
Olivera Gonzales, Percy
Author
dc.contributor.author
Dávalos, Juan Z.
Admission date
dc.date.accessioned
2020-04-25T22:32:44Z
Available date
dc.date.available
2020-04-25T22:32:44Z
Publication date
dc.date.issued
2020
Cita de ítem
dc.identifier.citation
Journal of Chemistry Volume 2020, Article ID 7157281, 9 pages
es_ES
Identifier
dc.identifier.other
10.1155/2020/7157281
Identifier
dc.identifier.uri
https://repositorio.uchile.cl/handle/2250/174124
Abstract
dc.description.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, (HNMR)-H-1, and C-13 NMR) techniques. The two-dimensionalNMR(in acetone-d(6)) spectral data revealed that the molecules 1 and 2 in solution are in the cisE isomeric form. This evidence is supported by DFTcalculations 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. 6ein vitro antibacterial activity of compounds 1-4 was determined against Grampositive (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 mu g/mL, respectively) and Bacillus subtilis (MIC = 100 and 150 mu 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.
es_ES
Patrocinador
dc.description.sponsorship
Universidad de Lima Scientific Research Institute
Comision Nacional de Investigacion Cientifica y Tecnologica (CONICYT), CONICYT PIA/BASAL: FB0807
Ministry of Science, Innovation, and Universities (MICINN). RTI2018-094356-B-C21
Cabildo de Tenerife (Agustin de Betancourt Program)