Design, Synthesis, and Biological Evaluation of Novel Pyrazole, Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone

The novel ligand (L) 1-(furanyl)-3-(pyrrolyl)propenone had been synthesized, and its novel chelates of some 3d series of transition metal ions had been prepared and characterized. The structural properties of the titled compounds were explored using elemental analyses, spectroscopic techniques (UV-visible, MS, and FT-IR), molar conductivity, and magnetic susceptibility measurements. The scanning electron microscope (SEM) showed that the ligand and its metal chelates exist in stick crystallized structures and sizes of their molecules can exist in nanoform. Thermal analyses techniques (TG and DTA) measured the investigated chelates during their thermal degradation to elucidate their structures. It was proved that ligand (L) acts as bibasic bidentate ligand coordinating to metal cations via its two oxygen atoms of carbonyl and epoxy groups. The optimization of the structural formula for the examined ligand had been performed by using Gaussian 09 program. The energy gaps were calculated using the DFT/B3LYP method. The ligand and its chelates had been fixed to have consistent bond lengths and bond angles that proved via quantum chemical factors. The ligand (L) and its transition metal chelates had been tested for their antibacterial activities. In vitro biological properties for ligand (L) and its transition metal complexes were carried out against Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) by agar diffusion technique.The results showed that title compounds are biologically active than the parent ligand in their sticks crystalline and possible nanostructures and consequently large surface interactions. Molecular docking showed favorable interaction between ligand and crystal structures of 3t88 E. coli, 3ty7 S. aureus, 5h67 B. subtilis, and 5i39 P. aeruginosa. This docking study proved that nanosize of ligand helps it to interact efficiently with proteins of bacteria.

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“…The bands occurring in the wavenumber range 400–415 cm −l are assigned due to stretching vibration of ν(M–O). [ 29–32 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, antimicrobial, and docking study of novel 1‐(furanyl)‐3‐(pyrrolyl)propenone‐based ligand and its chelates of 3d‐transition metal ions

Zayed

Radwan

et al. 2021

Applied Organom Chemis

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“…From the intensity of the 1 H-NMR spectrum, the ratio of NH signals to OH signals was (36:100) or ca (1:3). This means that the lactim form is more predominate in solution [21,23] (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…[15] It was worth mentioning that different pyridines and pyrazoles were noticed to have a significantly broad range of applications particularly as anticancer agents. [16,17] The sake of the current study is to construct a novel group of pyridine derivatives that might have biological activity as the continuation of our efforts [18][19][20][21][22][23][24] conducted in the direction of preparation of novel heterocyclic compounds with expected biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐cyano‐2‐pyridone derivative and its utility in the synthesis of some heterocyclic compounds with expecting antimicrobial activity

El‐Hashash

Shaban

Ali

2020

Journal of Heterocyclic Chem

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New 2‐pyridone derivatives bearing p‐methoxyphenyl and p‐bromophenyl substituents at C‐4 and C‐6 were prepared smoothly by the one‐pot reaction in high yield, and in a comparatively short time, it reacted with phosphorous oxychloride to produce the corresponding chloro compound. The latter was reacted with several nitrogen nucleophiles such as sodium azide, hydrazine, acetohydrazide, and benzohydrazide to give tetrazolo, hydrazino, and triazolo derivatives, respectively. The reaction of hydrazino derivative with cyclopentanone, furan‐2‐carbaldehyde afforded the corresponding hydrazone derivatives. Cyclocondensation of the latter compounds with thioglycolic acid afforded the nicotinamide derivatives. 2‐Pyridone reacted with ethyl chloroacetate to afford chloroacetate and ethyl acetate derivatives. Ethyl acetate‐derivative reacted with hydrazine hydrate and gave the acetohydrazide derivative, it was condensed with p‐anisaldehyde and gave the 4‐methoxybenzylidene acetohydrazide derivative. Also, 2‐pyridone reacted with chloroacetic acid and or benzoyl chloride, afforded the benzoate derivative and 2‐((6‐(4‐bromophenyl)‐3‐cyano‐4‐(4‐methoxyphenyl) pyridin‐2‐yl) oxy) acetic acid, respectively. Structures of the products were confirmed using spectroscopic data and elemental analyses. Antibacterial activity of the synthesized compounds was evaluated against Escherichia coli and Staphylococcus aureus.

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“…[ 20 ] Polysubstituted pyridine containing cyano group exhibited antitumor activity in numerous publications. [ 21–27 ] In addition, cyano pyridine derivatives have shown to possess promising anti‐microbial, [ 28–30 ] antioxidant, [ 31–33 ] antibiotic, [ 34–36 ] anti‐inflammatory, [ 37,38 ] analgesic, [ 39 ] anti‐convulsant, [ 40 ] and anticancer activities. [ 41 ] Also, pyridine is widely distributed in many biological molecules, and found in drugs such as nifedipine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

Raslan

Hessein

Fouad

et al. 2021

Journal of Heterocyclic Chem

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A novel series of thiazolo[5,4‐b]pyridine, polysubstituted pyridines, pyrazolo [3,4‐b] pyridine‐5‐carbonitriles, and polyhydroquinoline were synthesized via one‐pot reaction of 2‐iminothiazolidin‐5‐one, acetyl pyridine, pyrazolone, and/or cyclohexanone with various aldehydes, some active methylene and ammonium acetate in the presence of ceric ammonium nitrate (CAN). The resulting compounds were generated in high yields in a short amount of time, and the structures of the novel compounds were confirmed using IR, 1H NMR, 13C‐NMR, and mass spectra. The cytotoxic activity of 15 substances was tested in vitro against HePG‐2 and Caco‐2 cell lines. The results of antitumor assay confirmed that quinoline 12d compounds possess higher cytotoxic activity against two cell lines closed to doxorubicin, which is used as a standard anticancer drug. Also, 12c compounds are more efficient antitumor against the 2‐cell lines. While compounds 1 showed moderate activity toward Caco‐2. On the other hand, most of the tested compounds exhibited moderate to low cytotoxic activity toward the two cell lines. Based on the results, some of the newly synthesized derivatives showed excellent antitumor activity that qualified them for biomedical applications.

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Design, Synthesis, and Biological Evaluation of Novel Pyrazole, Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone

Cited by 40 publications

References 26 publications

Synthesis, characterization, antimicrobial, and docking study of novel 1‐(furanyl)‐3‐(pyrrolyl)propenone‐based ligand and its chelates of 3d‐transition metal ions

Synthesis, characterization, antimicrobial, and docking study of novel 1‐(furanyl)‐3‐(pyrrolyl)propenone‐based ligand and its chelates of 3d‐transition metal ions

Synthesis of 3‐cyano‐2‐pyridone derivative and its utility in the synthesis of some heterocyclic compounds with expecting antimicrobial activity

Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

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