Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities
Joint Authors
Hernández, Wilfredo
Spodine, Evgenia
Carrasco, Fernando
Chupayo, Oscar
Álvarez, Celedonio M.
Oramas-Royo, Sandra
Tamariz-Angeles, Carmen
Olivera-Gonzales, Percy
Dávalos, Juan Z.
Source
Issue
Vol. 2020, Issue 2020 (31 Dec. 2020), pp.1-9, 9 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2020-03-19
Country of Publication
Egypt
No. of Pages
9
Main Subjects
Abstract EN
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.
American Psychological Association (APA)
Carrasco, Fernando& Hernández, Wilfredo& Chupayo, Oscar& Álvarez, Celedonio M.& Oramas-Royo, Sandra& Spodine, Evgenia…[et al.]. 2020. Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities. Journal of Chemistry،Vol. 2020, no. 2020, pp.1-9.
https://search.emarefa.net/detail/BIM-1182141
Modern Language Association (MLA)
Carrasco, Fernando…[et al.]. Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities. Journal of Chemistry No. 2020 (2020), pp.1-9.
https://search.emarefa.net/detail/BIM-1182141
American Medical Association (AMA)
Carrasco, Fernando& Hernández, Wilfredo& Chupayo, Oscar& Álvarez, Celedonio M.& Oramas-Royo, Sandra& Spodine, Evgenia…[et al.]. Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities. Journal of Chemistry. 2020. Vol. 2020, no. 2020, pp.1-9.
https://search.emarefa.net/detail/BIM-1182141
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1182141