Study of the structure-bioactivity relationship of three new pyridine Schiff bases: Synthesis, spectral characterization, DFT calculations and biological assays

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Resumen

Schiff bases exhibit a broad range of applications, including their use as catalysts, stabilizers, dyes, and intermediates in organic synthesis; and biological activities, such as antifungal properties. In this work, we synthesized and characterized three new pyridine Schiff bases L3 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-chloro-phenol), L4 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-6-chloro-phenol), and L5 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4-methyl-phenol) to explore their structure-bioactivity relationship as antifungal agents. We also synthesized and characterized a diamine-derived Schiff base (L6) that is similar to (E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (L2, which previously demonstrated antifungal activity), but lacks the pyridine ring, to assess the impact of this structural modification on the biological properties. All the Schiff bases were characterized by FTIR, 1H and 13C NMR, DEPT, HHCOSY, TOCSY, UV-vis, MS, cyclic voltammetry, DFT calculations, and NBO to assess the stability of the intramolecular hydrogen bond (IHB). In addition, we determined the antimicrobial properties by obtaining the minimal inhibitory concentration (MIC) for Cryptococcus spp. (yeast) and Salmonella enterica (bacteria), and growth inhibition of Botrytis cinerea (mold). We found that the antifungal activity of these Schiff bases relied on the nitrogen atom in the pyridine ring, and the antifungal activity can be modulated by different substituents in the phenolic ring. In this work we provide data supporting a correlation between the structure and bioactivity in this kind of Schiff base. The understanding of the structural prerequisites for antimicrobial activity could contribute to designing new drugs.

IdiomaEnglish
Páginas8851-8863
Número de páginas13
PublicaciónNew Journal of Chemistry
Volumen42
Número de edición11
DOI
EstadoPublished - 1 ene 2018

Huella dactilar

Schiff Bases
Bioactivity
Discrete Fourier transforms
Pyridine
Phenols
Assays
Phenol
Antifungal agents
Stabilizers (agents)
Salmonella
Yeast
Cyclic voltammetry
Bacteria
Hydrogen bonds
Diamines
Dyes
Antifungal Agents
Nuclear magnetic resonance
Nitrogen
Atoms

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Citar esto

@article{0e1d52a358e2449b8a3a35cd10cb3ce4,
title = "Study of the structure-bioactivity relationship of three new pyridine Schiff bases: Synthesis, spectral characterization, DFT calculations and biological assays",
abstract = "Schiff bases exhibit a broad range of applications, including their use as catalysts, stabilizers, dyes, and intermediates in organic synthesis; and biological activities, such as antifungal properties. In this work, we synthesized and characterized three new pyridine Schiff bases L3 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-chloro-phenol), L4 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-6-chloro-phenol), and L5 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4-methyl-phenol) to explore their structure-bioactivity relationship as antifungal agents. We also synthesized and characterized a diamine-derived Schiff base (L6) that is similar to (E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (L2, which previously demonstrated antifungal activity), but lacks the pyridine ring, to assess the impact of this structural modification on the biological properties. All the Schiff bases were characterized by FTIR, 1H and 13C NMR, DEPT, HHCOSY, TOCSY, UV-vis, MS, cyclic voltammetry, DFT calculations, and NBO to assess the stability of the intramolecular hydrogen bond (IHB). In addition, we determined the antimicrobial properties by obtaining the minimal inhibitory concentration (MIC) for Cryptococcus spp. (yeast) and Salmonella enterica (bacteria), and growth inhibition of Botrytis cinerea (mold). We found that the antifungal activity of these Schiff bases relied on the nitrogen atom in the pyridine ring, and the antifungal activity can be modulated by different substituents in the phenolic ring. In this work we provide data supporting a correlation between the structure and bioactivity in this kind of Schiff base. The understanding of the structural prerequisites for antimicrobial activity could contribute to designing new drugs.",
author = "Alexander Carre{\~n}o and C{\'e}sar Z{\'u}{\~n}iga and Day{\'a}n P{\'a}ez-Hern{\'a}ndez and Manuel Gacit{\'u}a and Rub{\'e}n Polanco and Carolina Otero and Ramiro Arratia-P{\'e}rez and Fuentes, {Juan A.}",
year = "2018",
month = "1",
day = "1",
doi = "10.1039/c8nj00390d",
language = "English",
volume = "42",
pages = "8851--8863",
journal = "New Journal of Chemistry",
issn = "1144-0546",
publisher = "Royal Society of Chemistry",
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TY - JOUR

T1 - Study of the structure-bioactivity relationship of three new pyridine Schiff bases

T2 - New Journal of Chemistry

AU - Carreño,Alexander

AU - Zúñiga,César

AU - Páez-Hernández,Dayán

AU - Gacitúa,Manuel

AU - Polanco,Rubén

AU - Otero,Carolina

AU - Arratia-Pérez,Ramiro

AU - Fuentes,Juan A.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Schiff bases exhibit a broad range of applications, including their use as catalysts, stabilizers, dyes, and intermediates in organic synthesis; and biological activities, such as antifungal properties. In this work, we synthesized and characterized three new pyridine Schiff bases L3 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-chloro-phenol), L4 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-6-chloro-phenol), and L5 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4-methyl-phenol) to explore their structure-bioactivity relationship as antifungal agents. We also synthesized and characterized a diamine-derived Schiff base (L6) that is similar to (E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (L2, which previously demonstrated antifungal activity), but lacks the pyridine ring, to assess the impact of this structural modification on the biological properties. All the Schiff bases were characterized by FTIR, 1H and 13C NMR, DEPT, HHCOSY, TOCSY, UV-vis, MS, cyclic voltammetry, DFT calculations, and NBO to assess the stability of the intramolecular hydrogen bond (IHB). In addition, we determined the antimicrobial properties by obtaining the minimal inhibitory concentration (MIC) for Cryptococcus spp. (yeast) and Salmonella enterica (bacteria), and growth inhibition of Botrytis cinerea (mold). We found that the antifungal activity of these Schiff bases relied on the nitrogen atom in the pyridine ring, and the antifungal activity can be modulated by different substituents in the phenolic ring. In this work we provide data supporting a correlation between the structure and bioactivity in this kind of Schiff base. The understanding of the structural prerequisites for antimicrobial activity could contribute to designing new drugs.

AB - Schiff bases exhibit a broad range of applications, including their use as catalysts, stabilizers, dyes, and intermediates in organic synthesis; and biological activities, such as antifungal properties. In this work, we synthesized and characterized three new pyridine Schiff bases L3 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-chloro-phenol), L4 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-6-chloro-phenol), and L5 ((E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4-methyl-phenol) to explore their structure-bioactivity relationship as antifungal agents. We also synthesized and characterized a diamine-derived Schiff base (L6) that is similar to (E)-2-{[(3-aminopyridin-4-yl)imino]-methyl}-4,6-di-tert-butyl-phenol (L2, which previously demonstrated antifungal activity), but lacks the pyridine ring, to assess the impact of this structural modification on the biological properties. All the Schiff bases were characterized by FTIR, 1H and 13C NMR, DEPT, HHCOSY, TOCSY, UV-vis, MS, cyclic voltammetry, DFT calculations, and NBO to assess the stability of the intramolecular hydrogen bond (IHB). In addition, we determined the antimicrobial properties by obtaining the minimal inhibitory concentration (MIC) for Cryptococcus spp. (yeast) and Salmonella enterica (bacteria), and growth inhibition of Botrytis cinerea (mold). We found that the antifungal activity of these Schiff bases relied on the nitrogen atom in the pyridine ring, and the antifungal activity can be modulated by different substituents in the phenolic ring. In this work we provide data supporting a correlation between the structure and bioactivity in this kind of Schiff base. The understanding of the structural prerequisites for antimicrobial activity could contribute to designing new drugs.

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U2 - 10.1039/c8nj00390d

DO - 10.1039/c8nj00390d

M3 - Article

VL - 42

SP - 8851

EP - 8863

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 11

ER -