Green Synthesis of New Amino Acid Schiff Bases and Their Biological Activities

Yorur-Goreci, Cigdem; Demir, Zulal; Altaş, Nilay

doi:10.18596/jotcsa.14900

Cited by 3 publications

(3 citation statements)

References 13 publications

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“…The precipitated Schiff bases were filtered, washed with cold ethanol several times, and dried at room temperature. The solid products were then recrystallized with ethanol [ 31 ].…”

Section: Methodsmentioning

confidence: 99%

New Amino Acid Schiff Bases as Anticancer Agents via Potential Mitochondrial Complex I-Associated Hexokinase Inhibition and Targeting AMP-Protein Kinases/mTOR Signaling Pathway

et al. 2021

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Two series of novel amino acid Schiff base ligands containing heterocyclic moieties, such as quinazolinone 3–11 and indole 12–20 were successfully synthesized and confirmed by spectroscopic techniques and elemental analysis. Furthermore, all compounds were investigated in silico for their ability to inhibit mitochondrial NADH: ubiquinone oxidoreductase (complex I) by targeting the AMPK/mTOR signaling pathway and inhibiting hexokinase, a key glycolytic enzyme to prevent the Warburg effect in cancer cells. This inhibitory pathway may be an effective strategy to cause cancer cell death due to an insufficient amount of ATP. Our results revealed that, out of 18 compounds, two (11 and 20) were top-ranked as they exhibited the highest binding energies of −8.8, −13.0, −7.9, and −10.0 kcal/mol in the docking analysis, so they were then selected for in vitro assessment. Compound 11 promoted the best cytotoxic effect on MCF-7 with IC50 = 64.05 ± 0.14 μg/mL (0.135 mM) while compound 20 exhibited the best cytotoxic effect on MDA-231 with IC50 = 46.29 ± 0.09 μg/mL (0.166 mM) Compounds 11 and 20 showed significant activation of AMPK protein and oxidative stress, which led to elevated expression of p53 and Bax, reduced Bcl-2 expression, and caused cell cycle arrest at the sub-G0/G1 phase. Moreover, compounds 11 and 20 showed significant inhibition of the mTOR protein, which led to the activation of aerobic glycolysis for survival. This alternative pathway was also blocked as compounds 11 and 20 showed significant inhibitory effects on the hexokinase enzyme. These findings demonstrate that compounds 11 and 20 obeyed Lipinski’s rule of five and could be used as privileged scaffolds for cancer therapy via their potential inhibition of mitochondrial complex I-associated hexokinase.

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“…The precipitated Schiff bases were filtered, washed with cold ethanol several times, and dried at room temperature. The solid products were then recrystallized with ethanol [ 31 ].…”

Section: Methodsmentioning

confidence: 99%

New Amino Acid Schiff Bases as Anticancer Agents via Potential Mitochondrial Complex I-Associated Hexokinase Inhibition and Targeting AMP-Protein Kinases/mTOR Signaling Pathway

et al. 2021

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“…4-(1, 3-dioxoisoindolin-2-yl) benzohydrazide derivatives (3a-f) 15,16 Using a flask with a round bottom and a magnetic stirrer, each of the aldehydeslisted in further detail in Table 1 was dissolved in ethanol, adding three drops of glacial acetic acid.…”

Section: -(13-dioxoisoindolin-2-yl) Benzoyl Chloridementioning

confidence: 99%

Synthesis, characterization and preliminary antimicrobial study of some new phthalimide phenyl hydrazide derivatives

Alassadi,

Hadi

2024

F1000Res

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Background: The synthesis and antibacterial efficacy of phthalimide Schiff bases derivatives (3a-f) derived from phthalic anhydride were investigated. The aim of this study was to assess the antibacterial activity of the synthesized Schiff bases against five different types of microbes in vitro. Methods: The Schiff bases were synthesized by reacting various aldehydes with the hydrazine of phthalimidobenzoic acid. The compounds were identified using FTIR and 1HNMR spectroscopy studies, and their antibacterial efficacy against four bacterial species (Staphylococcus aureus, Streptococcus pyrogens, Escherichia coli, and Pseudomonas aeruginosa) and one fungal species (Candida albicans) was assessed in vitro using a 100 µg/mL concentration of derivatives in dimethyl sulfoxide. Results: The antimicrobial activity of each compound towards the isolates was variable. Most of the compounds exhibited a slight inhibition rate towards Gram-positive and Gram-negative bacteria, particularly S. aureus, which was shown to be highly resistant to all derivatives used. However, there was moderate to high killing activity towards S. pyogenes. Conclusions: The synthesized phthalimide Schiff bases derivatives exhibited variable antibacterial activity against the tested microbes. The results suggest that further studies are required to optimize the efficacy of these compounds against harmful microorganisms.

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“…The mixture was concentrated then allowed to cool. The precipitated Schiff base was filtered, washed with ethanol several times, and dried in the oven at 60 o C. The solid product was then stored under vacuum (23) .…”

Section: Synthesis Of Methyl 2-((4-(13-dioxoisoindolin-2yl) Benzylidmentioning

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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Green Synthesis of New Amino Acid Schiff Bases and Their Biological Activities

Cited by 3 publications

References 13 publications

New Amino Acid Schiff Bases as Anticancer Agents via Potential Mitochondrial Complex I-Associated Hexokinase Inhibition and Targeting AMP-Protein Kinases/mTOR Signaling Pathway

New Amino Acid Schiff Bases as Anticancer Agents via Potential Mitochondrial Complex I-Associated Hexokinase Inhibition and Targeting AMP-Protein Kinases/mTOR Signaling Pathway

Synthesis, characterization and preliminary antimicrobial study of some new phthalimide phenyl hydrazide derivatives

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

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