Enantioselective Henry reaction catalyzed by a novel L-(+)-aspartic acid-derived Schiff base ligand and Cu(II) ion

Koz, Gamze; Astley, Demet; Astley, Stephen T.

doi:10.3906/kim-1103-19

Cited by 3 publications

(4 citation statements)

References 1 publication

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“…We synthesized salicylidene uracils (5SU) with the reaction of 5aminouracil with substituted salicylaldehydes using well-known procedures. [36] A brief scheme of the compounds is presented in Table 1.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity

Poslu,

Aslan,

Koz

et al. 2023

Archiv der Pharmazie

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A series of salicylidene uracil (1–18) derived from 5‐aminouracil and substituted salicylaldehydes were analyzed for cytotoxic activity and enzyme inhibitory potency. Nine out of eighteen derivatives (6–8, 10, 12–15, 18) are novel molecules synthesized for the first time in this work, and other derivatives were previously synthesized by our group. The compounds were characterized by Proton nuclear magnetic resonance, carbon nuclear magnetic resonance, fourier transform infrared spectroscopy, and elemental analysis. All compounds were tested for their in vitro cytotoxicity against PC‐3 (human prostate adenocarcinoma), A549 (human alveolar adenocarcinoma), and SHSY‐5Y (human neuroblastoma) cancer cell lines and the nontumorigenic HEK293 (human embryonic kidney cells) cell line. The 3,5‐di‐tert‐butylsalicylaldehyde derived compound (8) was toxic to PC‐3 human prostate adenocarcinoma cells, showing a promising IC50 value at 7.05 ± 0.76 μM. The present study also aimed to evaluate the inhibitory effects of the compounds against several key enzymes, namely carbonic anhydrase I and II (CA I and CA II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and glutathione reductase (GR), which are implicated in various global disorders, such as Alzheimer's disease, epilepsy, cancer, malaria, diabetes, and glaucoma. The inhibitory profiles of the tested compounds were assessed by determining their Ki values, which ranged from 2.96 to 9.24 nM for AChE, 3.78 to 12.57 nM for BChE, 8.42 to 25.74 nM for CA I, 7.24 to 19.74 nM for CA II, and 0.541 to 1.124 μM for GR. Molecular docking studies were also performed for all compounds. Most derivatives exhibited much more effective inhibitory action compared with clinically used standards. Thus, our findings indicate that the salicylidene derivatives presented in this study are promising drug candidates that need further evaluation.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity

Poslu,

Aslan,

Koz

et al. 2023

Archiv der Pharmazie

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“…The synthesis, spectroscopic analysis, and investigation of the biological activity of Ni(II), Cu(II), and Co(II) complexes formed by Schiff base ligands derived from 5-aminouracil, 2-hydroxy-1naphthaldehyde, 2,4-dihydroxybenzaldehyde, and salic-ylaldehyde have been reported: [15]. In each instance, the complexes seem to exist as monomers.…”

Section: Synthesis Of Metal Complexes With Uracil and Its Derivativesmentioning

confidence: 99%

“…The in vitro testing of the biological activities of both Schiff bases and metal complexes was conducted against several bacteria and a fungus. [15]. Nickel(II) complexes, formed from the Schiff base ligand derived from salicylaldehyde, exhibited effective antimicrobial activity.…”

Section: Biological Activities Antibacterial Activitymentioning

confidence: 99%

Synthesis and Biological Activities of Some Metal Complexes of 2-Thiouracil and Its Derivatives: A Review

Marinova,

Tamahkyarova

2023

Preprint

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The thionamide antithyroid drugs were discovered largely following serendipitous observations by numerous researchers in the 1940s who found that sulfhydryl-containing compounds were goitrogenic in animals. Prof. Edwin B. Astwood was the first to use these compounds to treat hyperthyroidism. In this review, we summarize the history of the development of these drugs and the coordination possibility of 2-thiouracil and its derivatives, as well as the biological activities of some of its complexes. Some of them are used as agents for the treatment of tuberculosis, and arthritis, others have bactericidal and fungicidal activity, the third cytotoxic properties, and could be used to treat various types of cancer.

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“…The crystal structure of this novel 1D MOCP was established by the powder XRD analysis, its thermal stability was studied by thermogravimetric analysis (TGA), and its morphology was determined by FE-SEM measurements. It is well known that a number of Cu(II) complexes are effective as homogeneous [ 18 , 19 , 20 ] or heterogeneous catalysts [ 21 ] in Henry reactions (nitroaldol condensation). We intended to check the assumption that the [ Cu 2 (EDPB)•H 2 O] n material would operate as a catalyst in this process, due to Lewis base sites in amide moiety and Lewis acid sites as Cu 2+ ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and the Crystal Structure of a New Chiral 1D Metal–Organic Coordination Polymer Based on L-Prolineamide-Substituted Diarylacetylenedicarboxylic Acid Derivative

et al. 2022

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The new homochiral 1D metal–organic coordination polymer [Cu2(EDPB)•H2O]n was synthesized starting from the original 3,3′-ethyne-1,2-diylbis[6-(L-prolylamino)benzoic acid] (H4EDPB). The unique crystal structure of the new compound was established by powder X-ray diffraction. The [Cu2(EDPB)•H2O]n system shows catalytic activity and enantioselectivity in a Henry reaction of p-nitrobenzaldehyde with nitromethane.

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Enantioselective Henry reaction catalyzed by a novel L-(+)-aspartic acid-derived Schiff base ligand and Cu(II) ion

Cited by 3 publications

References 1 publication

Synthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity

Synthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity

Synthesis and Biological Activities of Some Metal Complexes of 2-Thiouracil and Its Derivatives: A Review

Synthesis and the Crystal Structure of a New Chiral 1D Metal–Organic Coordination Polymer Based on L-Prolineamide-Substituted Diarylacetylenedicarboxylic Acid Derivative

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