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Medicinal Chemistry Research

, Volume 28, Issue 1, pp 62–70 | Cite as

Synthesis and antimicrobial evaluation of novel N-substituted 4-ethylsulfanyl-2-pyridones and triazolopyridines

  • Rasha A. Azzam
  • Galal H. Elgemeie
Original Research
  • 43 Downloads

Abstract

The design and development of new methods for the synthesis of antimicrobial drugs is an important goal currently for medicinal chemistry. Sixteen novel N-substituted-amino-, N-arylsulfonylamino-, and N-aryl-4-ethylsulfanyl-2-pyridones were synthesized. Antimicrobial activities of the compounds were evaluated against four fungal and eight bacterial strains. Antimicrobial results showed that compound 14b had excellent activities as compared to all other newly synthesized compounds and a variety of standard ones against a variety of bacterial and fungal strains. Triazolo[1,5-a]pyridines 10c and 10e showed as well marked activities toward three of the tested Gram-negative bacteria.

Keywords

2-Pyridones N-cyanoacetohydrazide Cyanoaceto-N-phenylsulfonylhydrazide Antimicrobial activity 

Notes

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

References

  1. Abu-Zaied MA, El-Telbani EM, Elgemeie GH, Nawwar GA (2011) Synthesis and in vitro anti-tumor activity of new oxadiazole thioglycosides. Eur J Med Chem 46:211–229CrossRefGoogle Scholar
  2. Darwish ES, Atia KA, Farag AM (2014) Synthesis and antimicrobial evaluation of some isoxazole based heterocycles. Heterocycles 89:1393–1411CrossRefGoogle Scholar
  3. Desai NC, Rajpara KM, Joshi VV (2013) Synthesis of pyrazole encompassing 2-pyridone derivatives as antibacterial agents. Bioorg Med Chem Lett 23:2714–2717CrossRefGoogle Scholar
  4. Elgemeie GH (2003) Thioguanine, mercaptopurine, their analogs, and nucleosides as antimetabolites. Curr Pharm Des 9:2627–2642CrossRefGoogle Scholar
  5. Elgemeie GH, Abu-Zaied MA, Loutfy SA (2017) 4-Aminoantipyrine in carbohydrate research: design, synthesis and anticancer activity of a novel class of derivatives of 4-aminoantipyrine thioglycosides and their corresponding pyrazolopyrimidine and pyrazolopyridine thioglycosides. Tetrahedron 73:5853–5861CrossRefGoogle Scholar
  6. Elgemeie GH, Abu-Zaied MA, Nawwar GA (2018) First novel synthesis of triazole thioglycosides as ribavirin analogues. Nucleosides & Nucleotides 37:112–123CrossRefGoogle Scholar
  7. Elgemeie GH, El-Ezbawy SR, El-Aziz HA (2001) The design and synthesis of structurally related mercaptopurine analogues: reaction of dimethyl N-cyano-dithioiminocarbonate with 5-aminopyrazoles. Synth Commun 31:3453–3458CrossRefGoogle Scholar
  8. Elgemeie GH, Elghandor AH, Abd-Elaziz GW (2003) Novel synthesis of heterocyclic ketene N,N-, N,O-, and N,S-acetals using cyanoketene dithioacetals. Synth Commun 33:1659–1664CrossRefGoogle Scholar
  9. Elgemeie GH, Elghandor AH, Abd-Elaziz GW (2004) Potassium 2-cyanoethylene-1-thiolate: a new preparative route to 2-cyanoketene S,N-acetals and pyrazole derivatives. Synth Commun 34:3281–3291CrossRefGoogle Scholar
  10. Elgemeie GH, Elghandor AH, Elzanate AM, Ahamed SA (2006) Novel 1,3-dithiolanes using sodium α-cyano-ketene dithiolates. Synth Commun 36:755–764CrossRefGoogle Scholar
  11. Elgemeie GH, Elzanate AM, Elghandor AH, Ahamed SA (2002) Novel intramolecular cyclization of pyrazolone ketene S,N-acetals for the construction of methylsulfanylpyrazolo[4,3-b]pyridines. Synth Commun 32:3509–3517CrossRefGoogle Scholar
  12. Elgemeie GH, Jones PG (2002) N-[3-Cyano-2-oxo-5,6,7,8-tetrahydroquinoline-1(2H)-yl]-4-methylbenzenesulfonamide. Acta Cryst E58:1250–1251Google Scholar
  13. Elgemeie GH, Jones PG (2004) 6-Amino-4-(methylsulfanyl)-2-oxo-1-tolyl-1,2-dihydropyridine-3,5-dicarbonitrile. Acta Cryst E 60:2107–2109CrossRefGoogle Scholar
  14. Elgemeie GH, Jones PG (2016) Crystal structure of 1-amino-2-oxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[b]pyridine-3-carbonitrile. Acta Cryst E72:1239–1241Google Scholar
  15. Elgemeie GH, Mahmoud MA, Jones PG (2002) N-(3-Cyano-2-oxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[b]pyridin-1-yl)-4-methylbenzenesulfonamide. Acta Cryst E58:1293–1295Google Scholar
  16. Fassihi A, Abedi D, Saghaie L, Sabet R, Fazeli H, Bostaki G, Deilami O, Sadinpour H (2009) Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxy-pyridine-4-one and 3-hydroxypyran-4-one derivatives Eur J Med Chem 44:2145–2157. https://pubchem.ncbi.nlm.nih.gov/compound/391346(NSC690376), 391347 (NSC690377), 391348 (NSC690378), 391349 (NSC690379), 391350 (NSC690380), 391351 (NSC690381)CrossRefGoogle Scholar
  17. Li Q, Mitscher LA, Shen LL (2000) The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors. Med Res Rev 20:231–293CrossRefGoogle Scholar
  18. Maruza F, Chimenti F, Bolasco A, Filippelli A, Palla A, Filippelli W, Lampa E (1992) Antiinflammatory, analgesic and antipyfuztic 4,6-disubstituted 3-cyanopyridine-2-ones and 3-cyano-2-aminopyridines. Pharmacol Res 26:267–277CrossRefGoogle Scholar
  19. Shah NK, Shah NM, Patel MP, Patel RG (2013) Synthesis of 2-amino-4H-chromene derivatives under microwave irradiation and their antimicrobial activity‏. J Chem Sci 125:525–530CrossRefGoogle Scholar
  20. Wiegand I, Hilpert K, Hancock RE (2008) Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat Protoc 3:163–175CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Chemistry Department, Faculty of ScienceHelwan UniversityHelwanEgypt

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