Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides

El‐Sayed, Hassan A.; Moustafa, A. H.; Haikal, Abdelfattah; Abdou, Ibrahim M.; El-Ashry, E. S. H.

doi:10.1080/15257770802271805

Cited by 30 publications

(12 citation statements)

References 18 publications

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“…The IR spectrum revealed the absence of the amide carbonyl band, which indicated the formation of the O-ribofuranoside rather than the corresponding N-ribofuranoside derivative [7]. The deacetylation of the glycosides 13 and 14 and ribofuranoside 17 in the presence of methanol/TEA and a few drops of water [41][42][43] led to the formation of the free glycosides 15 and 16 and the ribofuranoside 18 (Scheme 4). The IR spectra of the resulting compounds exhibited broad bands at 3422, 3392 and 3450 cm 1 for the OH groups.…”

Section: Chemistrymentioning

confidence: 99%

“…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: 99%

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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“…3-Deazapyrimidine analogs produced significant growth inhibition against L-1210 leukemia cells in vitro and have shown antiviral activity against RNA viruses Shi and Schinazi, 2001;Abdou et al, 2002Abdou et al, , 2004El Sayed et al, 2008). However, the use of some anticancer drugs has led to the development of drug resistance, and some compounds are toxic (Shi and Schinazi, 2001;Reverdito et al, 2012).…”

Section: Introductionmentioning

confidence: 95%

Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides

Abdou

Rateb

Eldeab

2012

Heterocyclic Communications

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Two series of novel 3-cyano-2-(2 ″ ,3 ″ ,4 ″ -tri-Oacetyl-β -d -arabinopyranosyloxy)pyridones 5a -h and 9a,b were synthesized. Microwave irradiation has been used to obtain these products in high yield under milder conditions by the reaction of 2(1 H )-pyridone or its salt with an activated arabinose. The silyl method was used to obtain the same nucleosides 5a -h and 9a,b . Triethylamine was used to remove the acetyl protecting groups from the sugar moiety and to produce the free nucleosides 6a -h and 10a,b in 85 -91% yield.

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“…The improvement of the reaction rate, reaction selectivity, reaction yield, product purity and waste minimization are desired advantages of such green methods . Continuing for our application of the green techeniques in organic synthesis,‐ herein, we outline the synthesis of polyfunctional N ‐amino‐2‐oxonicotinonitriles and their sulfonamide candidates under ultrasound and microwave techeniques, in addition to evaluation of their antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Green Synthesis of Highly Substituted N‐Amino‐2‐oxo‐nicotinonitriles and Their Sulfonamide Derivatives under Ultrasonic and Microwave Irradiation

2019

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An efficient and facile approach has been described for the synthesis of a new series of 1‐amino‐2‐oxo‐nicotinonitriles and their sulfonamides under microwave and ultrasonic irradiation. The desired compounds 4 a‐l were obtained via condensation of p‐chlorobenzaldehyde, aryl or heteroaryl methyl ketone and cyanoacetohydrazide in the presence of catalytic piperidine under three synthetic methodologies (namely, conventional method, ultrasonic and microwave irradiation), the best results (short reaction times, pure products, high yield) were obtained by ultrasonic irradiation. Sulfonamides 5 a‐f resulted via reaction of amines 4 a‐e and 4 j with benzene sulfonyl chloride in the presence of pyridine. The synthesized compounds give no significant results when investigated against Gm (+ve) and Gm (‐ve) bacteria, and fungi strains.

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Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides

Cited by 30 publications

References 18 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

Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides

An Efficient and Green Synthesis of Highly Substituted N‐Amino‐2‐oxo‐nicotinonitriles and Their Sulfonamide Derivatives under Ultrasonic and Microwave Irradiation

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