Novel Ethyl 2-(1-aminocyclobutyl)-5-(benzoyloxy)-6-hydroxy-pyrimidine-4-carboxylate Derivatives: Synthesis and Anticancer Activities

Asha, D.; Kavitha, C.; Chandrappa, S.; Shivaramu, Prasanna D.; Vinaya, K.; Raghavan, Sathees C.; Rangappa, Kanchugarakoppal S.

doi:10.4236/jct.2010.11003

Cited by 3 publications

(1 citation statement)

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“…Cyclobutane, thiazole and thiazolidine derivatives, the synthesis of which is focused on here, and the structural and spectral characterization of new derivatives, have attracted attention in medicinal chemistry and biochemistry due to their wide range of various biological and pharmacological activities, including anti-microbial [1][2][3][4][5][6], anti-fungal [1,[7][8][9], anti-cancer [10][11][12][13] and anti-inflammatory [14][15][16] properties. These compounds, containing cyclobutane, thiazole and thiazolidine functions, appear to be suitable candidates for drug design.…”

Section: Introductionmentioning

confidence: 99%

Structure determination, vibrational bands and chemical shift assignments of 3-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)-2-(o-tolyl)thiazolidin-4-one: A combined experimental and quantum chemical density-functional theory studies

Şen

2019

Maced. J. Chem. Chem. Eng.

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This paper report is an analysis of the title compound by means of X-ray crystallography, FT-IR, NMR and DFT calculations, in the context of structural and spectral characterization. The crystal and molecular structures of the compound were determined by single-crystal X-ray diffraction (SCXRD). Fourier Transform Infrared (FTIR) spectrum was recorded in the range from 400 cm–1 to 4000 cm–1. The 1H and 13C nuclear magnetic resonance (NMR) spectra were also recorded. DFT calculations were employed to support X-ray molecular geometry and calculate IR and NMR (1H and 13C) spectral bands. The structural (bond lengths, bond angles, torsion angles) and spectral (vibrational modes and chemical shifts) parameters obtained from DFT levels (B3LYP/6-31G(d,p) and B3LYP/6-31G+(d,p)) were compared with experimental findings, and an excellent harmony between the two data was ascertained.

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Section: Introductionmentioning

confidence: 99%

Structure determination, vibrational bands and chemical shift assignments of 3-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)-2-(o-tolyl)thiazolidin-4-one: A combined experimental and quantum chemical density-functional theory studies

Şen

2019

Maced. J. Chem. Chem. Eng.

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Synthesis, X-ray structure analysis, thermodynamic and electronic properties of 4-acetamido benzaldehyde using vibrational spectroscopy and DFT calculations

Jasmine

Arunagiri²,

Subashini³

et al. 2017

Journal of Molecular Structure

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A Convenient and Practical Synthesis of Novel Pyrimidine Derivatives and its Therapeutic Potential

Arora,

Kumar,

Verma

2024

CBC

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Background:: A new series of 2-(2-(substituted aldehyde)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile analogs (1–19) was prepared by using the Biginelli reaction. background: A novel series of 2-(2-(substituted aldehyde)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile analogues (1–19) was synthesized using the Biginelli reaction Methods:: TLC was employed to ensure the progress and confirmation of the reactions. Silica gel G was employed as the stationary phase, and mobile phases such as chloroform: toluene and acetone: n-hexane were used for the synthesized compounds. NMR has characterized the synthesized compound. MS IR, CHN. Results:: The prepared derivatives were evaluated in vitro for antimicrobial activity against various bacteria and fungi using the tube dilution technique. Notably, compounds 2-(2-(3-Ethoxy-4- hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5- carbonitrile T1, 2-(2-(2-Hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6- dihydropyrimidine-5 carbonitrile T6, and 2-(2-(4-Hydroxybenzylidene)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T16, displayed significant antibacterial activity, surpassing the standard drug Ampicillin. In the antifungal category, compounds 2-(2-(3-Ethoxy-4-hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyri midine-5-carbonitrile T1, 2-(2-(3,4-Dimethoxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6- oxo-1,6-dihydropyrimidine-5-carbonitrile T2, and 2-(2-(2,4-Dichlorobenzylidene)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T13, were very much effective against both fungal strains A. niger as well as C. albicans. Furthermore, compounds 2-(2-(2- Hydroxybenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5 carbonitrile T6, 2-(2-(2-Nitrobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyri midine-5-carbonitrile T8, 2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo- 1,6-dihydropyrimidine-5-carbonitrile T12, and 2-(2-(4-Dimethylaminobenzylidene)hydrazinyl)-4-(2- chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T14 demonstrated remarkable antioxidant properties, because of their low IC50 values in the DPPH assay. In the realm of anticancer activity, 2-(2-(substituted aldehyde)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydro pyrimidine-5-carbonitrile T9 outperformed the standard drug Adriamycin in terms of its effectiveness against human lung cancer cells (A-549) with a GI50 value of less than 10 according to the SRB assay. In addition, the antidiabetic assessment highlighted the excellent performance of compounds 2-(2- (2-Nitrobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5- carbonitrile T8, 2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6- dihydropyrimidine-5-carbonitrile T12, and 2-(2-(3-Nitrobenzylidene)hydrazinyl)-4-(2-chloro phenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T15, with low IC50 values, when tested for their inhibition of α-amylase enzyme activity. Conclusions:: The synthesized derivatives demonstrated strong antimicrobial, antioxidant, anticancer, and antidiabetic properties when assessed using specific methods and compared to established drugs. Notably, compounds 2-(2-(3-Ethoxy-4-hydroxybenzylidene)hydrazinyl)-4-(2-chloro phenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T1, 2-(2-(2-Hydroxybenzylidene) hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5 carbonitrile T6, and 2- (2-(2,4-Dichlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine -5-carbonitrile T13, 2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-(2-chlorophenyl)-1-methyl-6-oxo- 1,6-dihydropyrimidine-5-carbonitrile T12 and 2-(2-(substituted aldehyde)hydrazinyl)-4-(2-chloro phenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile T9 exhibited even higher activity levels than the standard medications. The presence of electron-releasing groups in the synthesized compounds enhanced their antibacterial and antioxidant effects, particularly against B. subtilis. On the other hand, electron-withdrawing groups improved their anticancer and antidiabetic properties.

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Novel Ethyl 2-(1-aminocyclobutyl)-5-(benzoyloxy)-6-hydroxy-pyrimidine-4-carboxylate Derivatives: Synthesis and Anticancer Activities

Cited by 3 publications

References 33 publications

Structure determination, vibrational bands and chemical shift assignments of 3-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)-2-(o-tolyl)thiazolidin-4-one: A combined experimental and quantum chemical density-functional theory studies

Structure determination, vibrational bands and chemical shift assignments of 3-(4-(3-(2,5-dimethylphenyl)-3-methylcyclobutyl)thiazol-2-yl)-2-(o-tolyl)thiazolidin-4-one: A combined experimental and quantum chemical density-functional theory studies

Synthesis, X-ray structure analysis, thermodynamic and electronic properties of 4-acetamido benzaldehyde using vibrational spectroscopy and DFT calculations

A Convenient and Practical Synthesis of Novel Pyrimidine Derivatives and its Therapeutic Potential

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