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

Producción científica: Contribución a una revista › Artículo (Contribución a Revista) › revisión exhaustiva

20 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

Este resultado contribuye a los siguientes Objetivos de Desarrollo Sostenible

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Otros archivos y enlaces

QMI: Nuevos complejos de platino(II) y paladio(II) con derivados del furano-2-carbaldehído tiosemicarbazona y su actividad antitumoral
Hernández Gorritti, W. R. (Investigador principal), Carrasco Solis, F. C. (Investigador adjunto), Vaisberg, A. J. (Investigador adjunto), Spodine, E. (Investigador adjunto), Icker, M. (Investigador adjunto), Krautscheid, H. (Investigador adjunto) & Beyer, L. (Investigador adjunto)
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. Artículo 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",

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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 - 2090-9063

VL - 2020

SP - 1

EP - 9

JO - Journal of Chemistry

JF - 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

Acceder al documento

Otros archivos y enlaces

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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