Synthesis, Characterization and Antibacterial Studies of Some Isoniazid-derived Schiff Bases

Yong, Joseph N.; Mainsah, Evans N.; Ntum, Sally-Judith E.; Ndifon, Peter T.

doi:10.9734/irjpac/2016/27100

Cited by 6 publications

(10 citation statements)

References 4 publications

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“…is evidence confirms the formation of the hydrazones in these compounds [45]. For compounds 1, 2, and 3, the signals of the C-4 isoxazole aromatic carbons observed at δ � 106.85-104.31 were affected by the presence of the fluoro, methoxy, and chloro substituents in the C-2′ positions of the phenyl fragment bound to the isoxazole ring.…”

Section: Nmr Spectrasupporting

confidence: 62%

“…On the other hand, for compounds 6 (X � 4′-OCH 3 ), 7 (X � 4′-CH 3 ), and 8 (X � 4′-Cl), the CH�N proton signals are deshielded 0.21, 0.29, and 0.25 ppm, respectively, while the CONH proton signals are deshielded (0.6 and 0.68 ppm for 6 and 8, respectively) and shielded (0.21 ppm for 7) with respect the compound Nˈ-(4-(dimethylamino)benzylidene) isonicotinoylhydrazone monohydrate [45]. Besides, the signals of the CH proton of the isoxazole ring are deshielded 0.53, 0.46, and 0.79 ppm, respectively, with respect to the compound 3-bromo-N-(3-phenyl-5-isoxazolyl)propanamide [46].…”

Section: Nmr Spectramentioning

confidence: 98%

“…For compounds 1 and 3, the CH�N proton signals bound to the isoxazole phenyl group were affected by the presence of the fluoro and chloro substituents in the C-2′ positions of the aromatic ring, respectively. ese signals are deshielded 0.4 and 0.25 ppm, for 1 and 3, respectively, with respect to the imine proton of the compound N′-(4-(dimethylamino)benzylidene)isonicotinoylhy drazone monohydrate [45]. For compounds 1 (X � 2′-F), 2 (X � 2′-OCH 3 ), and 3 (X � 2′-Cl), the CONH proton signals are shielded 0.15 ppm and 0.21 ppm for 1 and 2, respectively, and deshielded 0.72 ppm (for 3) with respect to the chemical shift of the compound Nˈ-(4-(dimethylamino)benzylidene) isonicotinoylhydrazone monohydrate [45].…”

Section: Nmr Spectramentioning

confidence: 99%

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Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

Carrasco

Hernández

Chupayo

et al. 2021

Journal of Chemistry

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Eight new phenylisoxazole isoniazid derivatives, 3-(2′-fluorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (1), 3-(2′-methoxyphenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (2), 3-(2′-chlorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (3), 3-(3′-clorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (4), 3-(4′-bromophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (5), 5-(4′-methoxiphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (6), 5-(4′-methylphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (7), and 5-(4′-clorophenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (8), have been synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, and mass spectral data. The 2D NMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. This evidence is supported by computational calculations which were performed for compounds 1–8, using DFT/B3LYP level with the 6-311++G(d,p) basis set. The in vitro antituberculous activity of all the synthesized compounds was determined against the Mycobacterium tuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibited moderate bioactivity (MIC = 0.34–0.41 μM) with respect to the isoniazid drug (MIC = 0.91 μM) against the H37Rv sensitive strain. Compounds 6 (X = 4′-OCH3) and 7 (X = 4′-CH3) with MIC values of 12.41 and 13.06 μM, respectively, were about two times more cytotoxic, compared with isoniazid, against the resistant strain TB DM97.

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Section: Nmr Spectrasupporting

confidence: 62%

Section: Nmr Spectramentioning

confidence: 98%

Section: Nmr Spectramentioning

confidence: 99%

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Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

Carrasco

Hernández

Chupayo

et al. 2021

Journal of Chemistry

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“…The pale yellowish solid separated was filtered, washed several times with methanol,dried and stored over silica gel in a desiccated jar. It was recrystallized from DMF/ Methanol to give a shiny yellow powder (20) . Yield 81%; m.p.…”

Section: Synthesis Of N'-(4-(13-dioxoisoindolin-2-yl) Benzylidene) Imentioning

confidence: 99%

“…Many researchers condensed isoniazid with various aldehydes to produce Schiff bases with enhanced anti-tubercular and antimicrobial activities, For example, S. Syed Tajudeen et al (19) , produced Schiff base complexes of isoniazid with significantly enhanced antibacterial activity against microbial strains. As well as Joseph N. Yonge et al (20) , prepare disoniazid's Schiff bases by the reaction of isoniazid with pyridine carboxaldehyde which showed good activity agains tbacteria compared to isoniazid alone. No research work linked isoniazid with phthalimide moiety through Schiff base has been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Preliminary Biological Activity Evaluation of New N- Substituted Phthalimide Derivatives

Sahib

Mohammed²

2020

IJPS

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A A new series of bases of Schiff (H2-H4) derived from phthalic anhydrideweresynthesized. These Schiff bases were prepared by the reaction of different amines (tyrosine methyl ester, phenylalanine methyl ester, and isoniazid) with the phthalimide derived aldehyde with the aid of glacial acetic acid or triethylamine ascatalysts. All the synthesized compounds were characterized by (FT-IR and 1HNMR) analyses and were in vitro evaluated for their antimicrobial activity against six various kinds of microorganisms. All the synthesized compounds had been screened for their antimicrobial activity against two Gram-positive bacteria “Staph. Aureus, and Bacillus subtilis”, two Gram-negative bacteria “Escherichia coli, and Klebsiella pneumoniae”, and two fungi species “Candida tropicalis and Candida albicans” using concentrations of 62.5, 125 and 250 µg\mLof derivative in dimethyl sulfoxide(DMSO). All the synthesized compounds showed no activity at all against Gram-positive bacteria, for Gram-negative bacteria and fungi they showed moderate or no activity except compound H1revealedhigh antifungal activityagainstCandida tropicalisat concentrations 125 and 250 µg\ mL. Keywords: Schiff base, phthalic anhydride, antimicrobial.

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Spectroscopic studies, DFT calculations, cytotoxicity activity, and docking stimulation of novel metal complexes of Schiff base ligand of isonicotinohydrazide derivative

Mahmoud

Elsayed

Aboelnaga

et al. 2022

Applied Organom Chemis

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In this elucidation, the reactivity of isonicotinohydrazide derivative (3)(L) was reacted with the nitrate salts of Cr(III), Fe(III), Co(II), Ni(II), Cu(II), and Zn(II) to afford the corresponding stable metal coordination compounds. The synthesized metal coordination compounds were confirmed through physicochemical and analytical analysis such as elemental analysis, UV‐Visible, FT‐IR, TGA, Mass, 1H NMR, XRD, magnetic, and molar conductance analysis. All complexes exhibit distorted octahedral geometry except Zn(II) complex which has a distorted tetrahedral arrangement. Both the thermal stability and the kinetic parameter for all complexes were elucidated via TGA analysis and Coats‐Redfern method. XRD study suggested that the complexes have a partially amorphous structure which was further confirmed by calculating the crystallinity index. Moreover, the synthesized metal complexes exhibited excellent cytotoxicity activity contra lung cancer cells (A549) and liver cancer cells (HepG2) using neutral red uptake assay. The complexes of Fe(III), Ni(II), and Zn(II) showed higher cytotoxic effect than doxorubicin against A549 and HepG2 cells for 24 h incubation. Furthermore, the Cr(III), Co(II), Zn(II), and Cu(II) coordination compounds showed more inhibitory influence when treated with A549 and HepG2 cells for 48 h incubation. The biological studies of these complexes were confirmed through molecular docking studies with different proteins such as (PDB ID: 2ITO) and (PDB ID: 5H38) and showed low binding energy and shortage bond length with different amino acids. Also, computational calculations of all metal complexes were carried out utilizing DFT/B3LYP/LANL2DZ basis set to detect the FMO, ESP, MEP, and physical descriptor's of them and confirms their reactivity.

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Synthesis, Characterization and Antibacterial Studies of Some Isoniazid-derived Schiff Bases

Cited by 6 publications

References 4 publications

Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

Synthesis and Preliminary Biological Activity Evaluation of New N- Substituted Phthalimide Derivatives

Spectroscopic studies, DFT calculations, cytotoxicity activity, and docking stimulation of novel metal complexes of Schiff base ligand of isonicotinohydrazide derivative

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