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

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 journal › Article (Contribution to Journal) › peer-review

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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 contribution	Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas: Derivados del Indol-3-carbaldehído semicarbazona: síntesis, caracterización y actividades antibacterianas
Original language	English
Article number	7157281
Pages (from-to)	1-9
Number of pages	9
Journal	Journal of Chemistry
Volume	2020
DOIs	https://doi.org/10.1155/2020/7157281 https://doi.org/10.1155/2020/7157281 https://doi.org/10.1155/2020/7157281
State	Published - 1 Jan 2020

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Article

OECD Category

Ciencias naturales

Ulima Repository Category

Ciencias / Medicina y Salud

Ulima Repository Subject

Chemistry, Organic
Compuestos orgánicos
Organic compounds
Química orgánica

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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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. Article 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",

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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

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QMI: New complexes of platinum (II) and palladium (II) with derivatives of furan-2-carbaldehyde thiosemicarbazone and their antitumor activity

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

Abstract

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Ulima Repository Category

Ulima Repository Subject

UN SDGs

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QMI: New complexes of platinum (II) and palladium (II) with derivatives of furan-2-carbaldehyde thiosemicarbazone and their antitumor activity

Cite this