A series of pyridines and pyridine based sulfa-drugs as antimicrobial agents: Design, synthesis and antimicrobial activity

El‐Sayed, Hassan A.; Moustafa, A. H.; EL-Torky, Alaa; El-Salam, E. A. Abd

doi:10.1134/s107036321710022x

Cited by 30 publications

(11 citation statements)

References 21 publications

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“…All synthesized compounds showed moderate to good antibacterial and antifungal activities against tested strains, S. aureus , B. subtilis , E. coli , S. typhimurium , A. flavus , and C. albicans , as compared to standard reference drugs, Gentamycin and Ketoconazole. El-Sayed et al [ 81 ] reported that tetrazolo[1,5-a]pyridine derivative 193 and thienopyridine 194, synthesized from 6-ethoxy-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile, have good antimicrobial activities against S. aureus , B. cereus , E. coli , P. aeruginosa , A. flavus , and A. niger as compared to standard drugs, Cefotaxime and Dermatin ( Figure 19 ).…”

Section: Synthesis Of Fused Pyridines With Other Heterocycles With An...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 Fused Pyridines With Other Heterocycles With An...mentioning

confidence: 99%

Pyridine Compounds with Antimicrobial and Antiviral Activities

Marinescu

Popa

2022

IJMS

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“…Principally, pyridone containing nucleoside I and II is effective towards HL-60 and L1210 lymphoid leukemia cells, respectively [18][19][20]. In addition, 2-sulfanyl nicotinonitrile III [21] was reported to have antimicrobial activity against both pathogenic bacteria and fungi (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

A Direct Synthesis for a New Series of 2‐Oxo(thioxo)nicotinonitrile Nucleosides as Antimicrobial Agents

El‐Sayed

EL-Torky

Moustafa

2018

Journal of Heterocyclic Chem

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A facile synthesis of a new series of cyclic and acyclic nucleosides of polyfunctionalized 2‐oxo(thioxo)nicotinonitrile derivatives 1 and 2 was performed. Glycosylation of 2‐pyridone 1 and 2‐thiopyridone 2 with glycosyl/galactosyl bromides in the existence of KOH afforded the N‐nucleoside and S‐nucleoside analogues 3, 5, 7, and 9, respectively. Deacetylation of nucleosides 3, 5, 7, and 9 gave the deacetylated nucleosides 4, 6, 8, and 10, respectively. Alkylation of 2‐pyridone 1 with glycone analogues [namely, 4‐bromobutyl acetate, (2‐acetoxyethoxy)methyl bromide, 3‐chloropropane‐1,2‐diol, and allyl and / propargyl bromides] in the existence of K2CO3 afforded the corresponding O‐acyclic nucleoside analogues 11, 13, and 15–17, respectively. Finally, treating of compounds 11 and 13 with a small amount of Et3N tolerated the 6‐hydroxy deacetylated derivatives 12 and 14, respectively. The synthesized nucleosides and alkylated products were tested against Gram (+ve) (Staphylococcus aureus and Bacillus cereus) and (Pseudomonas aeruginosa and Escherichia coli) as Gram (−ve) and Fungi (Aspergillus flavus and Aspergillus niger) and showed moderate antibacterial and antifungal activity.

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“…In a previous study, we have found that the annulation of a new heterocyclic ring onto thieno[2,3‐ b ]pyridine systems increases its biological properties more than its base compound . Our recent studies have been in the development of new synthetic routes for a variety of heterocyclic ring systems utilizing simple available reagents with favorable pharmacological properties . This work describes an efficient and direct approach for heteroannulation of ethyl 3‐amino‐4,6‐diaryl‐thieno[2,3‐ b ]pyridine‐2‐carboxylate derivative 1 to tricyclic and tetracyclic pyridines and evaluation of their antibacterial properties.…”

Section: Introductionmentioning

confidence: 99%

Direct Synthesis of Multi‐functional Pyrimidine, Pyrazine, and Pyridine Scaffolds via Inter‐ and Intramolecular Annulations of 3‐Amino‐thieno[2,3‐b]pyridine‐2‐carboxylate

El‐Sayed

Said

2019

Journal of Heterocyclic Chem

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The synthesis of a new series of annulated thieno[2,3‐b]pyridines was performed. Ester compound 1 underwent heterocyclization upon reaction with phenylisothiocyanate and formamide to afford pyrimidines 2 and 3, respectively. Thienopyrimidine 5 was resulted via reaction of amino derivative 1 with triethyl orthoformate to afford the non‐isolable intermediate 4, which allowed hydrazinolysis with hydrazine hydrate to afford the target compound. Pyrimidine type 5 was condensed with p‐nitrobenzaldehyde to afford Schiff base 6. Refluxing of ester 1 with ethyl cyanoacetate and diethyl malonate followed by base‐mediated heterocyclization afforded condensed pyridines 8 and 9, respectively. The tetracyclic pyrazine derivative 14 was obtained from the reaction of amino compound 1 with 2,5‐dimethoxytetrahydrofuran followed by hydrazinolysis to give carbohydrazide 11, which undergo diazotization followed by Curtius rearrangement. The antibacterial results illustrated no significant results for the investigated compounds except compound 5, which has moderate activity against Gram‐positive bacteria.

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A series of pyridines and pyridine based sulfa-drugs as antimicrobial agents: Design, synthesis and antimicrobial activity

Cited by 30 publications

References 21 publications

Pyridine Compounds with Antimicrobial and Antiviral Activities

Pyridine Compounds with Antimicrobial and Antiviral Activities

A Direct Synthesis for a New Series of 2‐Oxo(thioxo)nicotinonitrile Nucleosides as Antimicrobial Agents

Direct Synthesis of Multi‐functional Pyrimidine, Pyrazine, and Pyridine Scaffolds via Inter‐ and Intramolecular Annulations of 3‐Amino‐thieno[2,3‐b]pyridine‐2‐carboxylate

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