Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles

Morsy, H. A.; Mohammed, Samar M.; Hamid, Atef M. Abdel; Moustafa, A. H.; El‐Sayed, Hassan A.

doi:10.1134/s1070428020010224

Cited by 5 publications

(3 citation statements)

References 17 publications

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“…Table 3 marked green the values identical to those of the standard medicines used, Ciprofloxacin and Miconazole. Morsy et al [ 58 ] synthesized 1,2,3-triazole nucleosides based on functionalized nicotinonitriles 131a – 131b and 132 , via [2 + 3]-dipolar-cycloaddition of terminal acetylenes 128a – 128b , 129 and 1-azidoglucose 130 ( Figure 13 ) in the presence of copper (I) ions generated from copper(II) sulfate and sodium L-(+)-ascorbate. Compounds 131a – 131b and 132 showed good in vitro antibacterial activity against Staphylococcus aureus ATCC 6538, Micrococci luteus ATCC 10240, Pseudomonas aeruginosa ATCC 9027, Escherichia coli ATCC 10536, Candida albicans ATCC 10231, and Aspergillus niger ATCC 16404.…”

Section: Synthesis Of Antimicrobial Pyridine Compounds Containing a F...mentioning

confidence: 99%

Pyridine Compounds with Antimicrobial and Antiviral Activities

Marinescu

Popa

2022

IJMS

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In the context of the new life-threatening COVID-19 pandemic caused by the SARS-CoV-2 virus, finding new antiviral and antimicrobial compounds is a priority in current research. Pyridine is a privileged nucleus among heterocycles; its compounds have been noted for their therapeutic properties, such as antimicrobial, antiviral, antitumor, analgesic, anticonvulsant, anti-inflammatory, antioxidant, anti-Alzheimer’s, anti-ulcer or antidiabetic. It is known that a pyridine compound, which also contains a heterocycle, has improved therapeutic properties. The singular presence of the pyridine nucleus, or its one together with one or more heterocycles, as well as a simple hydrocarbon linker, or grafted with organic groups, gives the key molecule a certain geometry, which determines an interaction with a specific protein, and defines the antimicrobial and antiviral selectivity for the target molecule. Moreover, an important role of pyridine in medicinal chemistry is to improve water solubility due to its poor basicity. In this article, we aim to review the methods of synthesis of pyridine compounds, their antimicrobial and antiviral activities, the correlation of pharmaceutical properties with various groups present in molecules as well as the binding mode from Molecular Docking Studies.

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Section: Synthesis Of Antimicrobial Pyridine Compounds Containing a F...mentioning

confidence: 99%

Pyridine Compounds with Antimicrobial and Antiviral Activities

Marinescu

Popa

2022

IJMS

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“…While 3-methylthiophen derivative inhibited M. luteus ATCC 10240 (35 mm) that was higher than standard (28 mm) at the concentration of 40 μg mL -1 . 29 In the library of 1,2,3-triazolyl-1,4-dihydropyridine hybrids, derivatives with methyl ester, ethyl ester, cyano, phenacyl, and benzyl functional group showed equipotent activity (10 μg mL -1 ) to the standard Tetracycline against Proteus mirabilis with MIC: 10 μg mL -1 . In more, cyano, phenacyl, and benzyl derivatives of 1,2,3-triazolyl-1,4dihydropyridine hybrids were equal potent against Escherichia coli with MIC: 30 μg mL -1 a nd more potent against Klebsiella pneumoniae (MIC: 8 μg mL -1 compared to reference drug (MIC: 10 μg mL -1 ).…”

Section: 23-triazole-14-dihydropyridine-35-dicarbonitrilesmentioning

confidence: 99%

Novel 1,2,3-triazole-1,4-dihydropyridine-3,5-dicarbonitrile derivatives: synthesis and antibacterial evaluation

Bhagwati¹,

Mehariya²,

Shah³

et al. 2021

ECB

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“…The second reason is the use of azide‐alkyne cycloaddition methodology in the synthesis of such moiety. Recently, our approaches are directed to development of new hybrid nicotinonitrile scaffolds with pharmacophore and fluorophore properties [18,23–27]. The current work describes an efficient synthetic click coupling between acetylenic nicotinonitrile and azidoacetamide aimed to form bacterially active hybrid molecules via 1,2,3‐triazole linker.…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of 4,6‐diarylnicotinonitrile‐acetamide hybrids via 1,2,3‐triazole linker as multitarget microbial inhibitors

El‐Sayed

Moustafa

masry

et al. 2021

Journal of Heterocyclic Chem

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An efficient and smart approach for design and synthesis of a novel series of nicotinonitrile‐1,2,3‐triazole‐acetamide hybrids was described. The synthetic methodology was commenced with preparation of acetylene derivatives via alkynylation of 2‐oxonicotinonitrile with propargyl bromide under mild basic catalyst (pot. carbonate). The facile click cycloaddition reaction of alkynes 2a‐f and azido‐acetamides 3‐5 in the presence of catalytic Cu(I) in H2O/tetrahydrofuran (THF) was utilized for the synthesis of target molecules 6a‐l. Triazoles 6c, d, f, and 6i have highly activity against the four pathogenic bacteria (Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, and Staphylococcus aureus) and two pathogenic fungi (Candida albicans and Aspergillus flavus) with minimum inhibitory concentration (MIC) in between 0.5 and 4 μg/ml for bacteria and 0.5 and 8 μg/ml for fungi.

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Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles

Cited by 5 publications

References 17 publications

Pyridine Compounds with Antimicrobial and Antiviral Activities

Pyridine Compounds with Antimicrobial and Antiviral Activities

Novel 1,2,3-triazole-1,4-dihydropyridine-3,5-dicarbonitrile derivatives: synthesis and antibacterial evaluation

An efficient synthesis of 4,6‐diarylnicotinonitrile‐acetamide hybrids via 1,2,3‐triazole linker as multitarget microbial inhibitors

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