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• DOI: 10.56726/irjmets31955
• Corpus ID: 44033361

BIOLOGICAL APPLICATION OF SCHIFF BASE AND ITS METAL COMPLEXES – A REVIEW

• Sunil Kumar Tobriya
• Published in International Research… 9 January 2023
• Biology, Chemistry

9 Citations

Review: a recent review in applications of heterocyclic compounds as antimicrobial agent, synthesis, characterization and anti-bacterial activity of schiff base and its mixed ligand complexes of cr (ii) and co (ii) containing vanillin and 2-aminophenol, synthesis, spectroscopic characterization, dft optimization and biological activities of schiff bases and their metal (ii) complexes, a novel azo-azomethine dye: synthesis, dyeing and antioxidant properties, synthesis, characterization and biological efficacies from some new dinuclear metal complexes for base 3-(3,4-dihydroxy-phenyl)-2-[(2-hydroxy-3-methylperoxy-benzylidene)-amino]-2-methyl propionic acid, antioxidant, biofilm inhibition and mutagenic activities of newly substituted fibrates, a review on the synthesis, characterization and application of schiff bases containing resorcinol moieties and their first row transition metal complexes, zn(ii) and pd(ii) complexes derived from novel benzohydrazide-based schiff base ligand as multi-target agents, effects of temperature, concentration and synergism on green schiff bases synthesized from vanillin in applications as corrosion inhibitors for carbon steel in well stimulation, 23 references, antibacterial evaluation of some schiff bases derived from 2-acetylpyridine and their metal complexes, synthesis, characterization and biological activity of schiff bases, synthesis, physical characterization and biological evaluation of schiff base m(ii) complexes, ruthenium(ii) complexes containing bidentate schiff bases and their antifungal activity, antifungal properties of schiff bases of chitosan, n-substituted chitosan and quaternized chitosan., synthesis of new vo(ii), co(ii), ni(ii) and cu(ii) complexes with isatin-3-chloro-4-floroaniline and 2-pyridinecarboxylidene-4-aminoantipyrine and their antimicrobial studies, co(ii) and cd(ii) complexes derived from heterocyclic schiff-bases: synthesis, structural characterisation, and biological activity, croatica chemica acta, current advances in antifungal targets and drug development., curcumin as a promising antifungal of clinical interest., related papers.

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• Published: 28 February 2014

Synthesis and characterization of Schiff's bases of sulfamethoxazole

• Zainab Hussain 1 ,
• Emad Yousif 2 ,
• Ahmed Ahmed 2 &
• Ali Altaie 1  

Organic and Medicinal Chemistry Letters volume  4 , Article number:  1 ( 2014 ) Cite this article

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Schiff's bases are excellent ligands which are synthesized from the condensation of primary amines with carbonyl groups.

The classical reaction for the synthesis of Schiff's bases in an ethanolic solution and glacial acetic acid as a catalyst was followed in the synthesis of substituted sulfamethoxazole compounds.

Conclusions

Some Schiff's bases containing sulfamethoxazole nucleus have been synthesized and characterized. The present compounds are hoped to be applied in the photostability of PVC.

Schiff's bases are an important class of organic compounds [ 1 ]. They were first reported by Hugo Schiff in 1864 [ 2 ]. Schiff's bases are condensation products of primary amines with carbonyl compounds. The common structural feature of these compounds is the azomethine group with the general formula RHC = N-R 1 , where R and R 1 are alkyl, aryl, cycloalkyl, or heterocyclic groups [ 1 ]. Structurally, a Schiff's base (also known as imine or azomethine) is a nitrogen analogue of an aldehyde or ketone in which the carbonyl group (>C = O) is replaced by an imine or azomethine group. Schiff's bases have also been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties [ 3 , 4 ]. Imine or azomethine groups are present in various natural, naturally derived, and nonnatural compounds. The imine group present in such compounds has been shown to be critical to their biological activities [ 5 – 7 ]. Schiff's bases are important compounds owing to their wide range of industrial applications [ 8 ]. Schiff's bases are used in the photostabilization of poly(vinyl chloride) polymers against photodegradation by ultraviolet radiation [ 9 – 11 ] and are also used to improve poly(methyl methacrylate) from degradation [ 12 ] and to prevent polystyrene from photodegradation by their addition to polymer films [ 13 , 14 ].

Fourier transform infrared (FTIR) spectra were registered on a SHIMADZU (8300, Kyoto, Japan) infrared spectrophotometer, using KBr discs. Proton nuclear magnetic resonance ( 1 H-NMR; 600 MHz) spectra were obtained at room temperature with Bruker equipment (Madison, WI, USA) using TMS as an internal standard in dimethyl sulfoxide (DMSO). Melting points were recorded using hot-stage Gallenkamp melting point apparatus (Loughborough, UK) and were uncorrected. Analytical grade chemicals (BDH, G.C.C., Hopkin & William Corporation, Poole, UK) were used throughout the project.

Results and discussion

The synthesis of Schiff's bases with different specific aldehydes in ethanol as a solvent and catalyst (glacial acetic acid) resulted in five new series of Schiff's bases with the general formula RHC = N-R 1 . Here R 1  = sulfamethoxazole and R = benzaldehyde, 4-bromobenzaldehyde, 2-hydroxybenzaldehyde (salicylaldehyde), 4 -N , N- dimethylbenzaldehyde, and 3-nitrobenzaldehyde were synthesized by the reaction of sulfamethoxazole and substituted aldehydes in ethanol (Scheme  1 ). Such compounds were characterized by different physicochemical techniques like melting point, elemental analysis, FTIR spectroscopy, and multinuclear NMR ( 1 H).

Scheme of the preparation of Schiff's bases from sulfamethoxazole. (1) 4-[(2-Hydroxy-benzylidene)-amino]- N -(5-methyl-isoxazol-3-yl)-benzene sulfonamide. (2) N -(5-Methyl-isoxazol-3-yl)-4-[(4-nitroox-benzylidene)-amino]-benzene sulfonamide. (3) 4-[(4-Dimethylamino-benzylidene)-amino]- N -(5-methyl-isoxazol-3-yl)-benzene sulfonamide. (4) 4-[(4-Bromo-benzylidene)-amino]- N -(5-methyl-isoxazol-3-yl)-benzene sulfonamide. (5) ( N -(5-Methyl-isoxazol-3-yl)-4-[(3-nitro-benzylidene)-amino]-benzene sulfonamide.

Physical properties of the prepared Schiff's bases

The physical properties of sulfamethoxazole and its derivatives including melting point, color, and elemental analysis are tabulated in Table  1 .

The structure of the prepared Schiff's bases was confirmed by infrared spectroscopy. The FTIR spectra of sulfamethoxazole and its prepared compounds, as shown in Table  2 , showed that the band of NH 2 was found in sulfamethoxazole in the location 3,298 cm −1 and then vanished. After that, the band of NH appeared in the prepared Schiff's bases with different shifting from 3,250 to 3,287 cm −1 . The band of C = N for imine stretching vibration was also not found in sulfamethoxazole, and it appeared in the prepared Schiff's bases with shifting from 1,603 to 1,650 cm −1 . Also, the band of C = N for ring stretching vibration shifted from 1,620 cm −1 in sulfamethoxazole to 1,615 to 1,630 cm −1 in the prepared compounds.

The ultraviolet-visible spectrophotometry technique is used to characterize sulfamethoxazole and its derivatives in DMSO as a solvent. The ultraviolet-visible electronic spectra of the prepared Schiff's bases showed absorption bands that could be attributed to π → π* electronic transitions; these transitions are assigned in relevance to the structures of the compounds. The electronic spectrum of sulfamethoxazole shows a band at the wavelength 280 nm; this may be attributed to the π → π* electronic transition. In the prepared Schiff's bases, the bands shifted to wavelengths different from that of the corresponding band in sulfamethoxazole, as shown in Table  3 , which appear in the wavelength range between 270 and 360 nm. These transitions may be attributed to π → π* and n  → π* electronic transitions.

The 1 H-NMR spectrum of compound (1) showed the following characteristic chemical shifts (DMSO as a solvent): the singlet signal at δ  = 2.212 ppm suggested the attribution of the protons of the CH 3 group, the singlet signal at δ  = 6.029 ppm suggested the attribution of the proton of CH of the isoxazole ring, the multiplet signal at δ  = 6.743 to 7.768 ppm suggested the attribution of the protons of two aromatic benzene rings, the singlet signal at δ  = 8.764 ppm suggested the attribution of the proton of the CH = N group, the singlet signal at δ  = 9.352 ppm suggested the attribution of the proton of the NH group, and the singlet signal at δ  = 10.525 ppm suggested the attribution of the proton of the OH group.

Also, the 1 H-NMR spectrum of compound (5) showed the following characteristic chemical shifts (DMSO as a solvent): the singlet signal at δ  = 2.200 ppm suggested the attribution of the protons of the CH 3 group, the singlet signal at δ  = 5.833 ppm suggested the attribution of the proton of CH of the isoxazole ring, the multiplet signal at δ  = 6.789 to 7.749 ppm suggested the attribution of the protons of two aromatic benzene rings, the singlet signal at δ  = 8.698 ppm suggested the attribution of the proton of the CH = N group, and the singlet signal at δ  = 9.602 ppm suggested the attribution of the proton of the NH group [ 15 ], as shown in Table  4 .

Experimental

A solution of sulfamethoxazole (0.001 mol) in absolute ethanol (30 ml) was slowly added to a solution of aldehyde (0.001 mol) in absolute ethanol (20 ml). The stirred reaction mixture was refluxed for 12 h. After cooling, a precipitate was formed which was collected by filtration, then washed with cold ethanol, and recrystallized from ethanol.

Five Schiff's bases: (1), (2), (3), (4), and (5), were synthesized as derivatives of sulfamethoxazole and characterized by UV, FTIR, and 1 H-NMR spectroscopies and elemental analysis (CHNS).

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Acknowledgements

The authors acknowledge the Department of Chemistry, College of Science, Al-Nahrain University for their encouragement.

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Department of Chemistry, College of Science for Women, Baghdad University, Baghdad, Iraq

Zainab Hussain & Ali Altaie

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Hussain, Z., Yousif, E., Ahmed, A. et al. Synthesis and characterization of Schiff's bases of sulfamethoxazole. Org Med Chem Lett 4 , 1 (2014). https://doi.org/10.1186/2191-2858-4-1

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Received : 05 January 2014

Accepted : 18 February 2014

Published : 28 February 2014

DOI : https://doi.org/10.1186/2191-2858-4-1

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SYNTHESIS OF SCHIFF BASES OF NOVEL INDOLES

Schiff bases are an important class of organic compounds. The common structural feature of these compounds have the azomethine group with the general formula RHC = N-R1, where R and R1 are alkyl, aryl, cycloalkyl, or heterocyclic groups. Schiff bases have also been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, antipyretic properties and also have some industrial applications. The imine group present in such compounds has been shown to be critical to their biological activities Schiff bases are synthesized by Sterker reaction in which condensation of primary aromatic amines with aryl aldehydes is found to be catalyzed by using mild catalysts in presence of organic solvent. Owing to vast applications of Schiff bases in field of medicine, agriculture and industry; the work presented here was carried out to synthesize indole based Schiff bases. Different substituted anilines and novel-indolic aldehyde are used to synthesize various kinds of imines using green procedure that doesn’t require excess of organic solvents. This eco-friendly reaction has many advantages like economical, medicinal, environmental and with mild reaction conditions, simple work-up yield high products.

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