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

doi:10.1155/2020/7157281

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

Título traducido de la contribución: Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas: Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas

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

Resultado de la investigación: Contribución a una revista › Artículo (Contribución a Revista) › revisión exhaustiva

4 Citas (Scopus)

Resumen

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.

Título traducido de la contribución	Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas: Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas
Idioma original	Inglés
Número de artículo	7157281
Páginas (desde-hasta)	1-9
Número de páginas	9
Publicación	Journal of Chemistry
Volumen	2020
DOI	https://doi.org/10.1155/2020/7157281 https://doi.org/10.1155/2020/7157281 https://doi.org/10.1155/2020/7157281
Estado	Publicada - 1 ene. 2020

COAR

Artículo

Categoría OCDE

Ciencias naturales

Categorías Repositorio Ulima

Ciencias / Medicina y Salud

Temas Repositorio Ulima

Chemistry, Organic
Compuestos orgánicos
Organic compounds
Química orgánica

ODS de las Naciones Unidas

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QMI: Nuevos complejos de platino(II) y paladio(II) con derivados del furano-2-carbaldehído tiosemicarbazona y su actividad antitumoral
Hernandez Gorritti, W. R., Carrasco Solis, F. C., Vaisberg, A. J., Spodine, E., Icker, M., Krautscheid, H. & Beyer, L.
1/04/21 → 31/03/22
Proyecto: Investigación

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Hernández, W., Carrasco, F., Chupayo, O., Álvarez, C. M., Oramas-Royo, S., Spodine, E., Tamariz-Angeles, C., Olivera-Gonzales, P., & Dávalos, J. Z. (2020). Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities. Journal of Chemistry, 2020, 1-9. [7157281]. https://doi.org/10.1155/2020/7157281, https://doi.org/10.1155/2020/7157281, https://doi.org/10.1155/2020/7157281

@article{d07c7b01e22c4d60981641b429b95475,

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

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), and2-((4-nitro-1H-indol-3-yl)methylene)hydrazinecarboxamide (4) were synthesized and characterized by ESI-MS and spectroscopic (FTIR, 1H NMR, and 13C NMR) techniques.6e two-dimensional NMR (in acetone-d6) spectral data revealed that the molecules 1 and 2 insolution are in the cisE isomeric form.6is evidence is supported by DFTcalculations at the B3LYP/6-311++G(d,p) level of theory whereit 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 and150 μg/mL, respectively) and Bacillus subtilis (MIC� 100 and 150 μg/mL, respectively). On the other hand, 3 and 4 were relatively lessactive against the tested bacterial strains compared with 1, 2, and tetracycline.",

author = "Wilfredo Hern{\'a}ndez and Fernando Carrasco and Oscar Chupayo and {\'A}lvarez, {Celedonio M.} and Sandra Oramas-Royo and Evgenia Spodine and Carmen Tamariz-Angeles and Percy Olivera-Gonzales and D{\'a}valos, {Juan Z.}",

note = "Publisher Copyright: {\textcopyright} 2020 Fernando Carrasco et al.",

year = "2020",

month = jan,

day = "1",

doi = "10.1155/2020/7157281",

language = "Ingl{\'e}s",

volume = "2020",

pages = "1--9",

journal = "New Journal of Chemistry",

issn = "1144-0546",

}

Hernández, W , Carrasco, F, Chupayo, O, Álvarez, CM, Oramas-Royo, S, Spodine, E, Tamariz-Angeles, C, Olivera-Gonzales, P & Dávalos, JZ 2020, 'Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities', Journal of Chemistry, vol. 2020, 7157281, pp. 1-9. https://doi.org/10.1155/2020/7157281, https://doi.org/10.1155/2020/7157281, https://doi.org/10.1155/2020/7157281

TY - JOUR

T1 - Indole-3-carbaldehyde Semicarbazone Derivatives

T2 - Synthesis, Characterization, and Antibacterial Activities

AU - Hernández, Wilfredo

AU - Carrasco, Fernando

AU - Chupayo, Oscar

AU - Álvarez, Celedonio M.

AU - Oramas-Royo, Sandra

AU - Spodine, Evgenia

AU - Tamariz-Angeles, Carmen

AU - Olivera-Gonzales, Percy

AU - Dávalos, Juan Z.

PY - 2020/1/1

Y1 - 2020/1/1

N2 - 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), and2-((4-nitro-1H-indol-3-yl)methylene)hydrazinecarboxamide (4) were synthesized and characterized by ESI-MS and spectroscopic (FTIR, 1H NMR, and 13C NMR) techniques.6e two-dimensional NMR (in acetone-d6) spectral data revealed that the molecules 1 and 2 insolution are in the cisE isomeric form.6is evidence is supported by DFTcalculations at the B3LYP/6-311++G(d,p) level of theory whereit 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 and150 μg/mL, respectively) and Bacillus subtilis (MIC� 100 and 150 μg/mL, respectively). On the other hand, 3 and 4 were relatively lessactive against the tested bacterial strains compared with 1, 2, and tetracycline.

AB - 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), and2-((4-nitro-1H-indol-3-yl)methylene)hydrazinecarboxamide (4) were synthesized and characterized by ESI-MS and spectroscopic (FTIR, 1H NMR, and 13C NMR) techniques.6e two-dimensional NMR (in acetone-d6) spectral data revealed that the molecules 1 and 2 insolution are in the cisE isomeric form.6is evidence is supported by DFTcalculations at the B3LYP/6-311++G(d,p) level of theory whereit 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 and150 μg/mL, respectively) and Bacillus subtilis (MIC� 100 and 150 μg/mL, respectively). On the other hand, 3 and 4 were relatively lessactive against the tested bacterial strains compared with 1, 2, and tetracycline.

UR - https://hdl.handle.net/20.500.12724/10791

UR - http://www.scopus.com/inward/record.url?scp=85082852043&partnerID=8YFLogxK

U2 - 10.1155/2020/7157281

DO - 10.1155/2020/7157281

M3 - Artículo (Contribución a Revista)

AN - SCOPUS:85082852043

SN - 1144-0546

VL - 2020

SP - 1

EP - 9

JO - New Journal of Chemistry

JF - New Journal of Chemistry

M1 - 7157281

ER -

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

Resumen

COAR

Categoría OCDE

Categorías Repositorio Ulima

Temas Repositorio Ulima

ODS de las Naciones Unidas

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Proyectos

QMI: Nuevos complejos de platino(II) y paladio(II) con derivados del furano-2-carbaldehído tiosemicarbazona y su actividad antitumoral

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