Schiff Bases: Interesting Scaffolds with Promising Antitumoral Properties (original) (raw)
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A review on Schiff base as a bioactive ligand
Purakala, 2020
Schiff bases are obtained from condensation of primary amines with carbonyl compounds. Schiff bases play an important role in inorganic chemistry due to formation of very stable complexes with various transition and inner-transition metals. There are several applications of Schiff bases in the field of biological activities which include antifungal, antimicrobial, antibacterial, anticancer, antioxidant, DNA cleavage, anti-inflammatory etc. Design of a new chemotherapeutic Schiff bases and their metal complexes is now attracting the attention of medicinal chemists. In this review article the biological applications of Schiff bases are summarized.
Applied Sciences
Metal complexes play an essential role in pharmaceutical sciences for their multiple and important activities. Schiff bases are versatile pharmacophores able to form chelating complexes with several metals in different oxidation states. Complexes with Schiff bases are widely described in the literature for their multiple actions and numerous advantages, such as low cost and easy synthesis. They show multiple biological activities, including antimicrobial, antioxidant, antimalarial, antinflammatory and antitumor. Schiff bases may also form complexes with lanthanides and actinides acting as catalysts (e.g., in various synthetic processes) and antitumor agents. This review intends to extend on our previous paper regarding Schiff bases as antitumorals, highlighting the importance, in the field of the anticancer agents, of these tools as ligands of metal complexes.
Synthesis, Characterisation And Antibacterial Activity Of Some New Schiff Bases
Solid State Technology Volume: 63 Issue: 6 Publication Year: , 2020
Schiff's bases are compounds of the aldehyde or ketone type in which the carbonyl group is replaced by an imine or azomethine group. It contains a carbon-nitrogen double bond with the nitrogen atom connected to an aryl or alkyl group but no hydrogen. Many metal complexes of Schiff bases have been studied to treat various bacterial, fungal, viral infections and neurological disorders. Metal complexes have a high place in pharmaceutical chemistry due to their different reactions to non-metals. Extensions of biological activity from the implementation of transition metals at Schiff bases have been reported. Schiff bases are widely used in analytical, organic and inorganic chemistry. Among azomethane derivatives, C = N connections are various natural (antistrocladidine has antimalarial activity), natural-derived (chitosin-derived shift bases have antifungal action) and non-compatible compounds required for biological activity. Many azomethanes have important antibacterial, antifungal, anticancer and diuretic activities. In addition to biological activities, finds application in many other fields such as organic synthesis, dyes, pigments, polymer stabilizers, corrosion inhibitors, fungicides, agrochemicals, analytical chemistry, electrical conductivity, magnetism, host guest chemistry and catalysis.Due to these important applications, we have synthesized various new Schiff bases and other heterocyclic compounds along with their characterisation (IR, 1HNMR and mass) and antibacterial evaluation on plant and human pathogenic bacterial strains. All the compounds showed excellent antibacterial activity against the pathogenic strains.
Biological Activities of Metal Complexes of Schiff Bases -A Review
Schiff bases have ability to form complexes with transition and inner transition metals and therefore regarded as very important class of organic compounds. Schiff bases serve as special ligands because they are readily synthesized by condensation reactions of aldehyde derivatives with imines. However their production is simple, their modest manufacturing technology and wide range of applications in areas such as coordination chemistry, analytical chemistry, catalysis and medicinal chemistry make them unique compounds. Various bioactivities such as anticancer, antineoplastic, analgesic, antifungal, antiviral, antioxidant, antibacterial, antipyretic, antiproliferative and anti-inflammatory etc. of schiff bases and their metal complexes are being studied. This review highlights synthesis as well as biological applications of various schiff bases and their metal complexes.
Synthesis, characterization, and anticancer activity of Schiff bases
2019
Five Schiff bases, 2-((3-chlorophenylimino)methyl)-5-(diethylamino)phenol (L1), 2-((2,4-dichlorophenylimino) methyl)-5-(diethylamino)phenol (L2), 5-(diethylamino)-2-((3,5-dimethylphenylimino)methyl)phenol (L3), 2-((2-chloro-4-methylphenylimino)methyl)-5-(diethylamino)phenol (L4), and 5-(diethylamino)-2- ((2,6-diethylphenylimino)methyl)phenol (L5) were synthesized and characterized by elemental analysis, FT-IR, 1H and 13C NMR spectroscopy. Three of the compounds (L1, L2, and L4) were analyzed by single crystal X-ray diffraction: L1 and L2 crystallized in orthorhombic P212121 and Pca21 space group, respectively, while L4 crystallized in monoclinic P21/c space group. Theoretical investigations were performed for all the synthesized compounds to evaluate the structural details. Drug–DNA interaction studies results from UV–Vis spectroscopy and electrochemistry complement that the compounds bind to DNA through electrostatic interactions. The cytotoxicity of the synthesized compounds was studied against cancer cell lines (HeLa and MCF-7) and a normal cell line (BHK-21) by means of an MTT assay compared to carboplatin, featuring IC50 values in the micromolar range. The pro-apoptotic mechanism for the active compound L5 was evaluated by fluorescence microscopy, cell cycle analysis, caspase-9 and -3 activity, reactive oxygen species production, and DNA binding studies that further strengthen the results of that L5 is a potent drug against cancer.
Performance of Schiff Bases Metal Complexes and their Ligand in Biological Activity: A Review
Al-Nahrain Journal of Science, 2021
Schiff bases are a broad class synthesized compound, which is prepared for the condensation process between the primary amine group and an aldehyde or ketone group. Schiff base metal complexes play an important role in many applications such as biological activity, catalytic activity, and optical property. The wide range application of Schiff base metal complexes came from the versatility of Schiff base reactions with many different transition metals. This flexibility of the reactions was given these complexes, many different properties and uses in a biological human system such as antibacterial, antifungal, anticancer, antimalarial, and others. This review gives many examples of Schiff bases, metal complexes, and there ligands with biological applications in the human system.
Synthesis and bioactivity studies of novel Schiff bases and their complexes
Journal of Physical Organic Chemistry, 2019
The new Schiff base (L) "4-[(2,4-dimethoxy-benzylidene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one" was synthesized from 2,4-dimethoxybenzaldehyde and 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one, and the geometry of Schiff base was characterized and determined by proton nuclear magnetic resonance (1 H-NMR), mass, Fourier transform infrared (FT-IR), and ultraviolet-visible (UV-vis) spectroscopy. Schiff complexes of Ni(II), Pd(II), Pt(IV), Zn(II), Cd(II), and Mg(II) have been prepared by reaction of ion metals with as-prepared Schiff base. The results showed that synthesized complexes offered 1:2 metal-ligand ratios. Furthermore, the Schiff complexes were a tetrahedral in complexes Ni(II), Zn(II), Cd(II), and Hg(II), octahedral Pt(II), and square planer complex Pd(II). Additionally, density functional theory (DFT) was applied for calculations of both spectroscopic properties and electronic structure of prepared Schiff bases. Moreover, the Schiff base and its metal complexes have been verified in vitro against Streptococcus, Esherichia coli, Candida albicans, and Candida tropicalis in order to assess their antibacterial potential. The findings indicate that the biological activity augments on complexation reaction.
Synthetic approaches of medicinally important Schiff bases: An updated Review
World Journal of Advanced Research and Reviews, 2022
The Schiff base defined by an imine or azomethine (-CH= N-) group, is mostly synthesized by the condensation reaction of carbonyl compounds (Aldehyde or Ketone) with compounds consisting of amine moiety. Schiff bases are among the most chiefly used organic compounds, revealing a wide range of applications, such as electroluminescent effects, fluorescence properties, nonlinear optical and chemosensory properties. The typical Schiff bases are crystalline solids that are basic, although at least some of them combine with strong acids to generate insoluble salt. Schiff bases are widely used in the pharmaceutical, electronic, cosmetic and polymer industries. Schiff bases use various alpha-amino acids and aldehydes in acidic or basic conditions. Schiff bases form a new class of drugs that can strengthen the immune system and also be used in the treatment of various ailments. The C=N imine bond's electrophilic carbon and nucleophilic nitrogen offer great binding chances with many nucleophiles and electrophiles, which can be used to suppress specific diseases, enzymes or DNA replication. These Schiff bases are synthesized from various aldehydes or ketones and amines under stirring conditions, catalyst-free, reflux conditions, conventional methods, microwave irradiation and ultrasonic conditions. Thus, Schiff bases and their derivatives can be synthesized using various techniques and may be further used for enormous biological applications with potent effects.
Open Access IJOC Biological Activities of Schiff Bases and Their Complexes: A Review of Recent Works
2013
Copyright © 2013 Wail Al Zoubi. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Schiff bases are the most widely used organic compounds. They have been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties. This review summarizes the synthesis and biological activities of Schiff bases and their complexes.