Chiral Schiff base ligands of salicylaldehyde: A versatile tool for medical applications and organic synthesis-A review

Jos, Saumya; Suja, N.R.

doi:10.1016/j.ica.2022.121323

Cited by 15 publications

(3 citation statements)

References 114 publications

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“…Salicylaldimine-derived chiral Schiff bases very easily coordinate with vanadium ions and exhibit widespread applications [11,12]. Among them, chiral Schiff bases derived from N-salicyl-β-amino alcohols are considered "privileged ligands" with fine-tuned structural and electronic properties [13,14]. Multidentate unsymmetrical vanadium(V) Schiff base complexes with such chiral ligands have been widely used as catalysts in the asymmetric alkynylation of aldehydes [15], enantioselective oxidation of organic sulfides [15][16][17], stereoselective synthesis of tetrahydrofurans [18,19], epoxidation of alkenes [20,21], and oxidation of bromide [18].…”

Section: Introductionmentioning

confidence: 99%

Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity

Romanowski,

Budka,

Inkielewicz-Stepniak

2024

IJMS

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Oxidovanadium(V) complexes, [(+)VOL1-5] and [(–)VOL1-5], with chiral tetradentate Schiff bases, which are products of monocondensation of S(‒)-3-amino-1,2-propanediol or R(+)-3-amino-1,2-propanediol with salicylaldehyde derivatives, have been synthesized. Different spectroscopic methods, viz. 1H and 51V NMR, IR, UV-Vis, and circular dichroism, as well as elemental analysis, have been used for their detailed characterization. Furthermore, the epoxidation of styrene, cyclohexene, and two monoterpenes, S(‒)-limonene and (‒)-α-pinene, using two oxidants, aqueous 30% H2O2 or tert-butyl hydroperoxide (TBHP) in decane, has been studied with catalytic amounts of all complexes. Finally, biological cytotoxicity studies have also been performed with these oxidovanadium(V) compounds for comparison with cis-dioxidomolybdenum(VI) Schiff base complexes with the same chiral ligands, as well as to determine the cytoprotection against the oxidative damage caused by 30% H2O2 in the HT-22 hippocampal neuronal cells in the range of their 10–100 μM concentration.

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Section: Introductionmentioning

confidence: 99%

Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity

Romanowski,

Budka,

Inkielewicz-Stepniak

2024

IJMS

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“…Chiral salen transition metal complexes have a significant role in the stereoselective synthesis being efficient chiral catalysts usable in a plethora of asymmetric transformations [ 1 , 2 , 3 , 4 ]. Their simple synthesis and the versatility in their structural modification have contributed to the current increased interest in the synthesis and characterization of new salen metal complexes [ 5 , 6 , 7 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Study of Catalytic Activity of Chiral Cu(II) and Ni(II) Salen Complexes in the α-Amino Acid C-α Alkylation Reaction

et al. 2023

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A new family of Cu(II) and Ni(II) salen complexes was synthesized and fully characterized through various physicochemical methods. Their catalytic activity was evaluated in the phase transfer Сα-alkylation reaction of the Schiff bases of D,L-alanine ester and benzaldehyde derivatives. It was found that the introduction of a chlorine atom into the ortho- and para-positions of the phenyl ring of the substrate resulted in an increase in both the chemical yield and the asymmetric induction (ee 66–98%). The highest enantiomeric excess was achieved in the case of a Cu(II) salen complex based on (S,S)-cyclohexanediamine and salicylaldehyde at −20 °C. The occurrence of a bulky substituent in the ligand present in the complexes led to a drastic decrease in ee and chemical yield. For instance, the introduction of bulky substituents at positions 3 and 5 of the phenyl ring of the catalyst resulted in a complete loss of the stereoselectivity control in the alkylation reaction.

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“…Schiff bases can be easily synthesized by a condensation reaction of different amino substituted compounds with versatile aldehydes or ketones [7]. Besides the fact that Schiff bases are important building blocks in medicinal chemistry due to their broad spectrum of biological activity [8][9][10][11][12], they have also been used in coordination chemistry [13][14][15], in analytical chemistry [16], as dyes [17], as optical chemosensors [18][19][20], as polymers [21], in catalysis [22], in metallurgy and refining of metals, and as fungicidal and agrochemical compounds. Additionally, the interest of numerous scientists is focused on evaluating Schiff bases as ligands for transition metals displaying diverse biological activities, such as anticancer [23,24], antimicrobial [25,26], and antifungal activities [27].…”

Section: Introductionmentioning

confidence: 99%

Novel Biologically Active N-Substituted Benzimidazole Derived Schiff Bases: Design, Synthesis, and Biological Evaluation

et al. 2023

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Herein, we present the design and synthesis of novel N-substituted benzimidazole-derived Schiff bases, and the evaluation of their antiviral, antibacterial, and antiproliferative activity. The impact on the biological activity of substituents placed at the N atom of the benzimidazole nuclei and the type of substituents attached at the phenyl ring were examined. All of the synthesized Schiff bases were evaluated in vitro for their antiviral activity against different viruses, antibacterial activity against a panel of bacterial strains, and antiproliferative activity on several human cancer cell lines, thus enabling the study of the structure−activity relationships. Some mild antiviral effects were noted, although at higher concentrations in comparison with the included reference drugs. Additionally, some derivatives showed a moderate antibacterial activity, with precursor 23 being broadly active against most of the tested bacterial strains. Lastly, Schiff base 40, a 4-N,N-diethylamino-2-hydroxy-substituted derivative bearing a phenyl ring at the N atom on the benzimidazole nuclei, displayed a strong antiproliferative activity against several cancer cell lines (IC50 1.1–4.4 μM). The strongest antitumoral effect was observed towards acute myeloid leukemia (HL-60).

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Chiral Schiff base ligands of salicylaldehyde: A versatile tool for medical applications and organic synthesis-A review

Cited by 15 publications

References 114 publications

Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity

Oxidovanadium(V) Schiff Base Complexes Derived from Chiral 3-amino-1,2-propanediol Enantiomers: Synthesis, Spectroscopic Studies, Catalytic and Biological Activity

Synthesis, Characterization, and Study of Catalytic Activity of Chiral Cu(II) and Ni(II) Salen Complexes in the α-Amino Acid C-α Alkylation Reaction

Novel Biologically Active N-Substituted Benzimidazole Derived Schiff Bases: Design, Synthesis, and Biological Evaluation

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