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

Wilfredo Hernández, Fernando Carrasco, Oscar Chupayo, Celedonio M. Álvarez, Sandra Oramas-Royo, Evgenia Spodine, Carmen Tamariz-Angeles, Percy Olivera-Gonzales, Juan Z. Dávalos

Research output: Contribution to journalArticle (Contribution to Journal)peer-review

4 Scopus citations

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 (FTIR, 1
H NMR, and 13C NMR) techniques.6e two-dimensional NMR (in acetone-d6) spectral data revealed that the molecules 1 and 2 in
solution are in the cisE isomeric form.6is 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.6e in vitro antibacterial activity of compounds 1–4was 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 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.
Translated title of the contributionDerivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas: Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas
Original languageEnglish
Article number7157281
Pages (from-to)1-9
Number of pages9
JournalJournal of Chemistry
Volume2020
DOIs
StatePublished - 1 Jan 2020

COAR

  • Article

OECD Category

  • Ciencias naturales

Ulima Repository Category

  • Ciencias / Medicina y Salud

Ulima Repository Subject

  • Chemistry, Organic
  • Compuestos orgánicos
  • Organic compounds
  • Química orgánica

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