A convenient synthesis of pyrrolo[2,3-b]pyridines and pyrido[2′,3′:5,4]pyrrolo[2,3-d]pyrimidines

Abdel‐Mohsen, Shawkat A.; Geies, A. A.

doi:10.1007/s00706-007-0839-3

Cited by 11 publications

(4 citation statements)

References 8 publications

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“…6‐Ethoxy‐2‐oxo(thioxo)‐4‐phenyl‐1,2‐dihydronicotinonitrile‐5‐carbonitrile ( 1 ) (Fig. ) was obtained according to the literature . Sulfurization of compound 1 with P 2 S 5 in pyridine furnished thioxo derivative 2 in high yield (91%) (Scheme ).…”

Section: Resultsmentioning

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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Section: Resultsmentioning

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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“…[91] The A lot of interest has been paid to pyrrolopyridines as an indole nucleus analog because of their intriguing biological properties. [92] Hence S.A. Abdel Mohsen and A.A. Geies synthesized the aforementioned series 42 a-i (Figure 11) and analyzed it for its biological activity. [93] Significant antibacterial activity was shown by compound 42 b against S. marcescens.…”

Section: Antimicrobialmentioning

confidence: 99%

“…[92] Hence S.A. Abdel Mohsen and A.A. Geies synthesized the aforementioned series 42 a-i (Figure 11) and analyzed it for its biological activity. [93] Significant antibacterial activity was shown by compound 42 b against S. marcescens. The compounds such as 42 k-l showed remarkable activity against S. aureus.…”

Section: Antimicrobialmentioning

confidence: 99%

Pharmacological Perspectives of 2‐alkoxy‐3‐Cyanopyridine Scaffolds: An Up‐to‐Date Review

Mahesha,

Shetty

2024

ChemistrySelect

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The 2‐alkoxy‐3‐cyanopyridine derivatives’ straightforward synthesis, ease of structural manipulation, and variety of intriguing biological activity continue to captivate medicinal chemists. A substantial body of research has demonstrated that these derivatives exhibit several intriguing biological characteristics, including anticancer, antibacterial, antidiabetic, antioxidant, vasorelaxant, antiviral, and anti‐inflammatory effects. Based on the basic skeleton of 2‐alkoxy‐3‐cyanopyridine, some lead compounds have been prepared with varied pharmaceutical characteristics. These served as excellent models for the development of novel medications since they showed potential in vitro and in vivo action against several cell lines that were both drug‐susceptible and drug‐resistant. To expand the use of 2‐alkoxy‐3‐cyanopyridine in biomedicine, though, a lot more efforts are essential. To combat medication resistance and boost specificity, potential hybrids that unite the 2‐alkoxy‐3‐cyanopyridine moiety with other pharmacophores are indeed required. This review offers a summary of pharmacological screening, including studies of pertinent structure‐activity connections, action mechanisms, and potential therapeutic use.

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“…Moreover, pyrido[2,3‐ d ]‐pyrimidine derivatives form a class of fused heterocyclic compounds, which have received considerable attention over the past years due to their wide range of biological activities such as analgesic , ulcerogenic , antianexiety , antimicrobial , antioxidant , antitumor , antiviral , cytotoxic , anti‐inflammatory , , antibacterial , antileishmanial activities and used as cyclin‐dependent kinase 4 (Cdk4) inhibitors . In addition, pyrrolo[2,3‐ b ]pyridine derivatives are of chemotherapeutic interest because they have been shown to act as antidiabetic , 5‐HT 6 receptor agonists or antagonists, useful for the treatment of central nervous system disorders , antitumor , and antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New [1,8]Naphthyridine, Pyrido[2,3‐d]‐Pyrimidine, and Other Annulated Pyridine Derivatives

El-Adasy

Khames

Gad‐Elkareem

2013

Journal of Heterocyclic Chem

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A convenient synthesis of pyrrolo[2,3-b]pyridines and pyrido[2′,3′:5,4]pyrrolo[2,3-d]pyrimidines

Cited by 11 publications

References 8 publications

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

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

Pharmacological Perspectives of 2‐alkoxy‐3‐Cyanopyridine Scaffolds: An Up‐to‐Date Review

Synthesis of Some New [1,8]Naphthyridine, Pyrido[2,3‐d]‐Pyrimidine, and Other Annulated Pyridine Derivatives

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