Purine and Guanine Thioglycoside Analogs: Novel Synthesis of a New Class of Pyrazolo[1,5-a][1,3,5]Triazine-4-Thioglycoside Derivatives under Microwave Activation

Elgemeie, Galal H.; Abu-Zaied, Mamdouh A.

doi:10.1080/15257770.2015.1078470

Cited by 21 publications

(5 citation statements)

References 16 publications

(27 reference statements)

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“…Nucleoside analogue inhibitors, currently used to treat viral infections, are chemically synthesized analogues of purines and pyrimidines in which the sugar moiety or heterocyclic ring has been altered. − Nucleoside analogues are managed as prodrugs, which are metabolized by host or viral kinases to their active triphosphate once inside the cell. Nucleoside analogues exert inhibitory effects on viral replication by one or more mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Anti-Covid-19 Drug Analogues: Synthesis of Novel Pyrimidine Thioglycosides as Antiviral Agents Against SARS-COV-2 and Avian Influenza H5N1 Viruses

2021

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A class of pyrimidine thioglycoside analogs ( 6a–h ) were synthesized from a reaction of 2-cyano-3,3-dimercapto- N -arylacrylamide ( 2a–d ) and thiourea to produce the corresponding 4-amino-2-mercapto- N -arylpyrimidine-5-carboxamide derivatives ( 3a–d ), and stirring of compounds ( 3a–d ) with peracylated α- d - gluco - and galacto-pyranosyl bromides ( 4a,b ) in DMF–sodium hydride gave the corresponding pyrimidine thioglycosides ( 5a–h ) . Deacetylation of the pyrimidine thioglycosides via a reaction with dry NH 3 /MeOH gave the corresponding free pyrimidine thioglycosides ( 6a–h ) . The compounds have been characterized by 13 C NMR, 1 H NMR, and IR. Pharmacological evaluation of compounds 3a–d , 5a–h , and 6a–h in vitro against SARS-COV-2 and Avian Influenza H5N1 virus strains revealed that some compounds possess interesting activity.

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Section: Introductionmentioning

confidence: 99%

Anti-Covid-19 Drug Analogues: Synthesis of Novel Pyrimidine Thioglycosides as Antiviral Agents Against SARS-COV-2 and Avian Influenza H5N1 Viruses

2021

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“…Heterocyclic compounds containing pyrazole rings are also efficacious components in many multi-component syntheses (Tu et al, 2014); we have reported and reviewed their use as novel synthetic intermediates Abu-Zaied et al, 2018Metwally et al, 2024). We have also synthesized various pyrazole-fused heterocyclic compounds as bioactive agents acting as antimetabolites (Elgemeie & Abu-Zaied, 2015;Elgemeie et al 2017aElgemeie et al ,b, 2019Mohamed-Ezzat & Elgemeie, 2023).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-N-(4-bromophenyl)-2-cyano-3-[3-(2-methylpropyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enamide

Abu-Zaied,

Mohamed-Ezzat,

Elgemeie

et al. 2024

Acta Crystallogr E Cryst Commun

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The structure of the title compound, C23H21BrN4O, contains two independent molecules connected by hydrogen bonds of the type Namide—H...N[triple-bond]C to form a dimer. The configuration at the exocyclic C=C double bond is E. The molecules are roughly planar except for the isopropyl groups. There are minor differences in the orientations of these groups and the phenyl rings at N1. The dimers are further linked by ‘weak’ hydrogen bonds, two each of the types Hphenyl...O=C (H...O = 2.50, 2.51 Å) and Hphenyl...Br (H...Br = 2.89, 2.91 Å), to form ribbons parallel to the b and c axes, respectively. The studied crystal was a non-merohedral twin.

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“…The reaction proceeded smoothly with microwave‐assisted protocol optimized with mild acidic medium (acetic acid) without observation of any side products (Scheme 21). The product 53 was further engaged in coupling with sugars to prepare purine thioglycosides [30a] …”

Section: Microwave‐assisted Chemistry Of Poly‐aza‐heterocyclesmentioning

confidence: 99%

The Riveting Chemistry of Poly‐aza‐heterocycles Employing Microwave Technique: A Decade Review

et al. 2021

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The application of microwave technique in chemical laboratory rooted back in 1986 and found advantageous over conventional approaches. On the other side, poly‐aza‐heterocycles are influencing organic frameworks with a fascinating chemistry and well explored by employing microwave‐assisted organic reactions. In the present review, we have thoroughly updated rousing literatures of microwave‐assisted synthesis and reactions of various poly‐aza‐heterocycles viz., triazole, tetrazole, triazine, and tetrazine from the past decade (2010–2020). The expedient chemistry and enabling role of microwave heating for adequate chemical transformations of such heterocycles, which were more challenging using classical approaches, are appropriately elucidated. This review also highlights the potential applications of these heterocyclic scaffolds and their derivatives in different scientific domains. Remarkably, such chemical architects possess wide applications as crucial building blocks in synthesis of biologically relevant compounds, agrochemicals, and compounds of interest in material science.

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Purine and Guanine Thioglycoside Analogs: Novel Synthesis of a New Class of Pyrazolo[1,5-a][1,3,5]Triazine-4-Thioglycoside Derivatives under Microwave Activation

Cited by 21 publications

References 16 publications

Anti-Covid-19 Drug Analogues: Synthesis of Novel Pyrimidine Thioglycosides as Antiviral Agents Against SARS-COV-2 and Avian Influenza H5N1 Viruses

Anti-Covid-19 Drug Analogues: Synthesis of Novel Pyrimidine Thioglycosides as Antiviral Agents Against SARS-COV-2 and Avian Influenza H5N1 Viruses

Crystal structure of (E)-N-(4-bromophenyl)-2-cyano-3-[3-(2-methylpropyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enamide

The Riveting Chemistry of Poly‐aza‐heterocycles Employing Microwave Technique: A Decade Review

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