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Synthesis of 2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide-based azetidinone derivatives as potent antibacterial and antifungal agents

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Abstract

Twelve compounds belonging to series N-[3-chloro-2-oxo-4-(substituted)phenylazetidin-1-yl]-2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide (5a–l) were synthesized. These compounds were evaluated for their in vitro antibacterial against E. coli, S. aureus, K. pneumoniae, P. aeruginosa and antifungal activity against C. albicans, A. niger and A. flavus by cup-plate method. Structures of all the newly synthesized compounds were confirmed by their spectral data interpretation. Compound 5g having p-dimethylaminophenyl group on 4-position of azetidinone ring attached to N-atom of acetamido group on 1-position of 3-methyl-1H-quinoxaline-2-one, was found to be active against all the bacterial and fungal strains under investigation.

A new series of compounds belonging to N-[3-chloro-2-oxo-4-(substituted) phenylazetidin-1-yl]-2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide was synthesized and all the newly synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities.

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References

  1. Grande F, Aiello F, Grazia O D, Brizzi A, Garofalo A and Neamati N 2007 Bioorg. Med. Chem. 15 288

    Article  CAS  Google Scholar 

  2. Amin K M, Ismail M M F, Noaman E, Soliman D H and Ammar Y A 2006 Bioorg. Med. Chem. 14 6917

    Article  CAS  Google Scholar 

  3. Zarranz B, Jaso A, Aldana I and Monge A 2004 Bioorg. Med. Chem. 12 3711

    Article  CAS  Google Scholar 

  4. Lee H, Cho S, Namgoong K, Jung JK and Yang S 2004 Bioorg. Med. Chem. Lett. 14 235

    Article  Google Scholar 

  5. Diana P, Martorana A, Barraja P and Montalbaro A 2008 J. Med. Chem. 51 2387

    Article  CAS  Google Scholar 

  6. Chung H J, Jung O J, Chae M J, Hong S Y, Chung K H and Lee SK 2005 Bioorg. Med. Chem. Lett. 15 3380

    Article  CAS  Google Scholar 

  7. Katsuyuki A, Obata T, Yamazaki Y, Mori Y, Hirokawa H, Koseki J, Hattori T, Niitsu K, Takeda S, Aburada M and Miyamoto K 2007 Chem. Pharm. Bull. 55 255

    Article  Google Scholar 

  8. Carta A, Loriga M, Paglietti G, Mattana A, Fiori PL, Mollicotti P, Sechi L and Zanetti S 2004 Eur. J. Med. Chem. 39 195

    Article  CAS  Google Scholar 

  9. Carta A, Paglietti G, Nikookar M E R, Sanna P, Sechi L and Zanetti S 2002 Eur. J. Med. Chem. 37 355

    Article  CAS  Google Scholar 

  10. Tandon V K, Yadav D B, Maurya H K, Chaturvedi A K and Shukla P K 2006 Bioorg. Med. Chem. 14 6120

    Article  CAS  Google Scholar 

  11. Kotharkar S A and Shinde D B 2006 Bioorg. Med. Chem. Lett. 16 6181

    Article  CAS  Google Scholar 

  12. Mashevskaya I V, Makhmudov R R, Aleksandrova G A, Golovnira O V, Duvalov A V and Maslivets A N 2001 Pharm. Chem. J. 35 196

    Article  CAS  Google Scholar 

  13. Mashevskaya I V, Tolmacheva I A, Voronova E V, Odegova T F, Alkeksandrova G A, Goleneva A F, Kot’tsova S V and Maslivets A N 2002 Pharm. Chem. J. 36 86

    Article  CAS  Google Scholar 

  14. Vyas D A, Chauhan N A and Parikh A R 2007 Indian J. Chem. 46B 1699

    CAS  Google Scholar 

  15. Jaso A, Zarranz B, Aldana I and Monge A 2003 Eur. J. Med. Chem. 38 791

    Article  CAS  Google Scholar 

  16. Zarranz B, Jaso A, Aldana I and Monge A 2003 Bioorg. Med. Chem. 11 2149

    Article  CAS  Google Scholar 

  17. Jaso A, Zarranz B, Aldana I and Monge A 2005 J. Med. Chem. 48 2019

    Article  CAS  Google Scholar 

  18. Seitz L E, Suling W J and Reynolds R C 2002 J. Med. Chem. 45 5604

    Article  CAS  Google Scholar 

  19. Burguete A, Pontiki E, Litina D H, Villar R, Vicente E, Solano B, Ancizu S, Aldana I and Monge A 2007 Bioorg. Med. Chem. Lett. 17 6439

    Article  CAS  Google Scholar 

  20. El-Bendary E R, Goda F E, Maaronf A R and Badria F A 2004 Sci. Pharm. 72 175

    CAS  Google Scholar 

  21. Cerić H, Šindler-Kulyk M, Kovačević M, Perić M and Živković A 2010 Bioorg. Med. Chem. 18 3053

    Article  Google Scholar 

  22. Patel J A, Mistry B D and Desai K R 2008 Indian J. Chem. 47B 1695

    CAS  Google Scholar 

  23. Kumar S, Khan S A, Alam O, Azim R, Khurana A, Shaquiquzzaman M, Siddiqui N and Ahsan W 2011 Bull. Korean Chem. Soc. 32 2260

    Article  Google Scholar 

  24. Zarei M and Mohamadzadeh M 2011 Tetrahedron 67 5832

    Article  CAS  Google Scholar 

  25. Abell A D and Oldham M D 1999 Bioorg. Med. Chem. Lett. 9 497

    Article  CAS  Google Scholar 

  26. Annunziata R, Benaglia M, Cinquini M, Cozzi F and Puglisi A 2002 Bioorg. Med. Chem. 10 1813

    Article  CAS  Google Scholar 

  27. Mehta P D, Sengar N P S and Pathak A K 2010 Eur. J. Med. Chem. 45 5541

    Article  CAS  Google Scholar 

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Correspondence to SHIV KUMAR.

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KUMAR, S., KUMAR, N., DRABU, S. et al. Synthesis of 2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide-based azetidinone derivatives as potent antibacterial and antifungal agents. J Chem Sci 125, 129–139 (2013). https://doi.org/10.1007/s12039-012-0354-x

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  • DOI: https://doi.org/10.1007/s12039-012-0354-x

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