Synthesis of Some New Pyrimidine Derivatives of Expected Antimicrobial Activity

Moustafa, A. H.; Saad, Hosam A.; Shehab, Wesam S.; El-Mobayed, M.

doi:10.1080/10426500701557286

Cited by 31 publications

(16 citation statements)

References 14 publications

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“…The formation of the O-glycoside 13 and O-galactoside 14 and not the corresponding N-glycoside derivatives were proven by 13 C NMR spectra, which revealed the presence of the anomeric carbons at 93.20 and 94.70 ppm, as well as the absence of a carbonyl amide band at 1645 cm 1 in the IR spectra [7]. Additionally, the reaction of 1 with preacetylated ribose under microwave irradiation [43] gave the ribofuranosyl derivative 17 (Scheme 4). The 1 H NMR spectrum of 17 exhibited signals at 2.00, 2.03 and 2.06 ppm from the three acetoxy groups and a doublet at 6.23 ppm from the anomeric proton with J = 3.80 Hz, which confirmed the -configuration of compound 17.…”

Section: Chemistrymentioning

confidence: 97%

“…The deacetylation of 9 and 11 was conducted in methanol in the presence of TEA and a few drops of water to produce the free acyclonucleosides 10 and 12 at a high yield [42][43][44] (Scheme 3). The 1 H NMR spectrum of compound 9 displayed signals at 1.72 and 1.79 ppm as a multiplet characteristic of CH 2(c) and CH 2(b) in addition to two triplets at 4.05 and 4.43 ppm that were characteristic of OCH 2(a) and CH 2 OCO (d) , respectively.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Biological Activity of Some Nucleoside Analogs of 3-Cyanopyridin-2- one

Saad¹,

Abdel‐Hafez²

2012

COS

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The pyridine derivative 3-cyano-4-(4-isopropylphenyl)-6-(pyridin-2-yl)-1H-pyridine-2-one 1 was obtained via the reaction of 2-acetylpyridine with cuminaldehyde and ethyl cyanoacetate in the presence of ammonium acetate. The pyridine-2-one 1 reacted with different alkyl halides, namely, allyl bromide, propargyl bromide, methyl bromoacetate, epichlorohydrin, 3-chloro-1-propanol, 1,3-dichloro-2-propanol, 4-bromobutyl acetate and 2-(bromomethoxy)ethyl acetate to give the corresponding nicotinonitrile Oacyclonucleosides 2-9 and 11, respectively. Subsequently, 9 and 11 were deacetylated to give the corresponding deprotected acyclonucleosides 10 and 12, respectively. In contrast, 4-(4-isopropylphenyl)-2-(2 ,3 ,4 ,6 -tetra-O-acetyl--D-gluco(galacto)pyranosyloxy)-6-(pyridin-2-yl)nicotinonitrile 13, 14, riboside 17 and lactoside 19 were prepared by the reaction of 1 with glycosyl/galactosyl/lactosyl bromide and peracetylated ribose using conventional and microwave irradiation methods. The reaction was regioselective and yielded the O-glycosides instead of the expected N-glycosides. The glycosides 13 and 14, riboside 17, and lactoside 19 were deacetylated in the presence of Et3N/MeOH and a few drops of water to give 15, 16, 18 and 21, respectively. The structure of the newly synthesized compounds was confirmed using IR, 1 H and 13 C NMR spectra, mass spectra and microanalysis. All synthesized compounds showed high antibacterial activity but the antifungal activity shown only by the glycoside compounds. Also, some of the new compounds showed anticancer activities.

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Section: Chemistrymentioning

confidence: 97%

Section: Chemistrymentioning

confidence: 99%

Synthesis and Biological Activity of Some Nucleoside Analogs of 3-Cyanopyridin-2- one

Saad¹,

Abdel‐Hafez²

2012

COS

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“…The title compounds 8(aj) were synthesized in five sequential steps using different reagents and reaction conditions (Figures 2 and 3), the 8(a-j) were obtained in moderate yields. The structure was established by spectral (IR, 1 H-NMR, 13 C-NMR and mass) and analytical data. …”

Section: Methodsmentioning

confidence: 99%

“…Flash chromatography was performed with silica gel (200-300 mesh) by using the mobile phase indicated. The NMR spectra were measured with a 400 MHz Bruker Avance spectrometer at 400.1 and 100.6 MHz, for 1 H for 13 C, respectively, in CDCl 3 solution with tetra methyl silane as internal standard. Chemical shifts are given in ppm (δ) and are referenced to the residual proton resonances of the solvents.…”

Section: Methodsmentioning

confidence: 99%

“…There exist three possible types of fusion of thiophene to pyrimidines ring results in corresponding isomeric thienopyrimidines namely; thieno [2,3-d] pyrimidines, thieno [3,4-d] pyrimidines and thieno [3,2-d] pyrimidines. Thieno pyrimidine derivatives, which are structure analogues of purines, have been focus of great interest because of their large range of pharmacological activities [1] as antibacterial, [2,3] antifungal [4], analgesic [5][6][7], antipyretic [8,9], anti-inflammatory [10], antihistaminic [11,12] anti-cancer [13][14][15] radioprotective [16,17]. Many thieno [2,3-d] pyrimidine derivatives were reported as phosphodiesterase inhibitors [18], also exhibited good H 1 receptor antagonistic activities [19], 4-amino derivatives showed insecticidal, pesticidal and acaricidal activities [20].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Structural Elucidation of Novel Thieno [2,3-d] Pyrimidine Core Unit Containing 1,2,4-Triazoles and Thiophenes as Potent Antimicrobial Activity

Prabhakar¹,

Kondra²,

Maddula³

2016

Organic Chem Curr Res

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Synthesis, Characterization, Antimicrobial Screening, and Computational Studies of a Tripodal Schiff Base Containing Pyrimidine Unit

Oruma

Ukoha

Rhyman

et al. 2018

Journal of Heterocyclic Chem

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A novel tripodal Schiff base ligand, 5‐amino‐2,4,6‐tris(4‐carboxybenzimino)‐1,3‐pyrimidine (TTPS), was synthesized for the first time by the reaction of 2,4,5,6‐tetraaminopyrimidine with 4‐carboxybenzaldehyde. The ligand was characterized by means of ultraviolet–visible, Fourier transform infrared, one‐dimensional 1H‐NMR, and one‐dimensional 13C‐NMR spectroscopies and elemental microanalysis. The Fourier transform infrared and NMR studies revealed that one of the NH2 group in 2,4,5,6‐tetraaminopyrimidine is not involved in bonding. The in vitro antimicrobial activities of the ligand were investigated against Gram‐negative bacteria: Escherichia coli (ATCC 6749) and Pseudomonas aeruginosa (ATCC 9027), Gram‐positive bacteria: Staphylococcus aureus (ATCC 6538P) and Bacillus cereus (ATCC 14579), and fungi: Candida albicans and Aspergillus niger by the agar well diffusion technique. TTPS exhibits good activity against the test microorganisms. The minimum inhibitory concentrations of TTPS against S. aureus were compared with tetracycline and gentamicin, which are conventional bacterial drugs. The upper level of Lorke's method was used to determine the acute toxicity of the compound. The acute toxicity test indicates that TTPS is toxic at doses above 2154 mg/kg. The in vivo antimalarial assay was carried out on Plasmodium berghei based on the 4‐day suppressive method. The result shows a general dose‐dependent significant parasitemia inhibition compared with the negative control with TTPS having inhibition of 72.20% at 50 mg/kg and 65.81% at 25 mg/kg close to the value (87.22%) of the standard drug artesunate 5 mg/kg. Density functional theory method was used to complement this experimental investigation.

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Synthesis of Some New Pyrimidine Derivatives of Expected Antimicrobial Activity

Cited by 31 publications

References 14 publications

Synthesis and Biological Activity of Some Nucleoside Analogs of 3-Cyanopyridin-2- one

Synthesis and Biological Activity of Some Nucleoside Analogs of 3-Cyanopyridin-2- one

Synthesis, Structural Elucidation of Novel Thieno [2,3-d] Pyrimidine Core Unit Containing 1,2,4-Triazoles and Thiophenes as Potent Antimicrobial Activity

Synthesis, Characterization, Antimicrobial Screening, and Computational Studies of a Tripodal Schiff Base Containing Pyrimidine Unit

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