Journal of Chemical Sciences

, Volume 129, Issue 10, pp 1549–1557 | Cite as

Expeditious synthesis of coumarin-pyridone conjugates molecules and their anti-microbial evaluation

  • Rajni Khajuria
  • Sheena Mahajan
  • Ambica
  • Kamal K Kapoor
Regular Article


An expedient synthesis of coumarin-pyridone conjugate molecules 2a-o is reported via one-pot reaction between (E)-3-(3-arylacryloyl)-2H-chromen-2-ones 1a-o, ethyl 2-nitroacetate and ammonium acetate. The structures of synthesized compounds have been unambiguously confirmed by spectroscopic analyses (NMR, IR and MS). All the compounds were screened for their anti-microbial activities against three Gram-positive bacterial strains, two Gram-negative bacterial strains and four fungal organisms. Compounds 2d, 2i, 2k, 2o exhibited mild anti-bacterial activity and 2d, 2m were found to be moderately active against all the tested fungal organisms. Compound 2k showed good inhibitory potential against the tested yeasts organisms.

Graphical Abstract

Expedient synthesis of coumarin-pyridone conjugate molecules has been reported via one-pot, three-component reaction between (E)-3-(3-arylacryloyl)-2H-chromen-2-ones, ethyl 2-nitroacetate and ammonium acetate. Anti-microbial activity of these compounds was evaluated and the results indicated that some of the compounds exhibited mild anti-bacterial activity and good inhibitory potential against the tested fungal organisms.


(E)-3-(3-arylacryloyl)-2H-chromen-2-ones ethyl 2-nitroacetate 6-(2-oxo-2H-chromen-3-yl)-4-arylpyridin-2(1H)-ones anti-bacterial anti-fungal 



The authors are thankful to Department of Chemistry, University of Jammu for providing all necessary facilities, Department of Science and Technology, GOI, New Delhi for funding (Project No. SR/S1/OC-38/2010) and NMR facility under PURSE.

Supplementary material

12039_2017_1362_MOESM1_ESM.docx (2.5 mb)
Supplementary material 1 (docx 2545 KB)


  1. 1.
    Kennedy R O and Thornes R D 1997 In Coumarins Biology, Applications and Mode of Action (New York: Wiley) p. 333Google Scholar
  2. 2.
    Hoult J R S and Paya M 1996 Pharmacological and biochemical actions of simple coumarins natural products with therapeutic potential Gen. Pharmacol. 27 713CrossRefGoogle Scholar
  3. 3.
    Musiciki B, Periers A M, Laurin P, Ferroud D, Benedetti Y, Lachaud S, Chatreaux F, Haesslein J L, ILtis A, Pierre C, Khider J, Tessol N, Airault M, Demassey J, Dupuis-Hamelin C, Lassaigne P, Bonnefoy A, Vicat P and Klich M 2000 Improved antibacterial activities of coumarin antibiotics bearing 5’,5’-dialkylnoviose: biological activity of RU79115 Bioorg. Med. Chem. Lett. 10 1695CrossRefGoogle Scholar
  4. 4.
    Rehman S U, Chohan Z H, Gulnaz F and Supuran C T 2005 In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes J. Enzyme Inhibit. Med. Chem. 20 333CrossRefGoogle Scholar
  5. 5.
    Kidane A G, Salacinski H, Tiwari A, Bruckdorfer K R and Seifalian A M 2004 Anticoagulant and antiplatelet agents: their clinical and device application(s) together with usages to engineer surface Biomacromolecules 5 798CrossRefGoogle Scholar
  6. 6.
    Kontogiorgis C A and Hadjipavlou-Litina D J 2004 Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage Bioorg. Med. Chem. Lett. 14 611CrossRefGoogle Scholar
  7. 7.
    Sashidhara K V, Rosaiah J N, Kumar A, Bhatia G and Khanna A K 2010 Synthesis of novel benzocoumarin derivatives as lipid lowering agents Bioorg. Med. Chem. Lett. 20 3065CrossRefGoogle Scholar
  8. 8.
    Kostova I 2005 Synthesis and Natural Coumarins as Cytotoxic Agents Curr. Med. Chem. 5 29Google Scholar
  9. 9.
    Weber U S, Steen B and Siegers C P 1998 Antitumor-activities of coumarin, 7-hydroxy-coumarin and its glucuronide in several human tumor cell lines Res. Commun. Mol. Pathol. Pharmacol. 99 193Google Scholar
  10. 10.
    Hamama W S, Waly M, El-Hawary I and Zoorob H H 2014 Developments in the Chemistry of 2-Pyridone Synth. Commun. 44 1730CrossRefGoogle Scholar
  11. 11.
    Li Q, Mitscher L A and Shen L L 2000 The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors 20 231CrossRefGoogle Scholar
  12. 12.
    Singh B, Bacon E R, Robinson S, Fritz R K and Lesher G U 1994 Novel cAMP PDE III inhibitors: imidazo [4,5-\(b\)-ones and their analogs J. Med. Chem. 37 248CrossRefGoogle Scholar
  13. 13.
    Hanfeld V, Leistner S, Wagner G, Lohmann D, Poppe H and Heer S 1988 Synthesis of 3-substituted 6-methyl-4-pyridyl-2 (1H) pyridones and testing of their cardiovascular action Pharmazie 43 677Google Scholar
  14. 14.
    Wagner G, Vieweg H and Leistner S 1993 Synthesis of new pyrido-(3’,2’:4,5)-thieno-(3,2-d)-1,2,3-triazine derivatives as anti-anaphylactics Pharmazie 48 576Google Scholar
  15. 15.
    Pierce J B, Ariyan Z S and Ovenden G S 1982 Preparation and antiinflammatory activity of 2- and 4-pyridones J. Med. Chem. 25 131CrossRefGoogle Scholar
  16. 16.
    Nagle P S, Pawar Y A, Sonawane A E, Bhosale S M and More D H 2012 Synthesis and evaluation of antioxidant and antimicrobial properties of thymol containing pyridine moieties Med. Chem. Res. 21 1395CrossRefGoogle Scholar
  17. 17.
    Breinhold J, Ludvigsen S, Rassing B R, Rosendahl C N, Nielsen S E and Olsen C E 1997 Oxysporidinone: a novel, antifungal N-methyl-4-hydroxy-2-pyridone from Fusarium oxysporum J. Nat. Prod. 60 33CrossRefGoogle Scholar
  18. 18.
    Lv Z, Sheng C, Wang T, Zhang Y, Liu J, Feng J, Sun H, Zhong H, Niu C and Li K 2010 Design, synthesis and antihepatitis B virus activities of novel 2-pyridone derivatives J. Med. Chem. 53 660CrossRefGoogle Scholar
  19. 19.
    Thorsett E D and Latimer L H 2000 Therapeutic approaches to Alzheimer’s disease Curr. Opin. Chem. Biol. 4 377CrossRefGoogle Scholar
  20. 20.
    Sashidhara K V, Kumar A, Kumar M, Sarkar J and Sinha S 2010 Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents Bioorg. Med. Chem. Lett. 20 7205CrossRefGoogle Scholar
  21. 21.
    Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C and Hadjipavlou-Litina D J 2009 Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts Eur. J. Med. Chem. 44 3020CrossRefGoogle Scholar
  22. 22.
    Song H Y, Ngai M H, Song Z Y, MacAry P A, Hobley J and Lear M 2009 Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides J. Org. Biomol. Chem. 7 3400CrossRefGoogle Scholar
  23. 23.
    Khajuria R, Kannaboina P, Kapoor K K, Gupta A, Raina G, Jassal A K, Rana L K, Hundal M S and Das P 2015 Divergent synthesis of 4, 6-diarylatedpyridin-2(1\(H)\)-ones from chalcones: Novel access to 2, 4, 6- triarylpyridines Org. Biomol. Chem. 13 5944CrossRefGoogle Scholar
  24. 24.
    Jayashree B S, Yusuf S and Kumar D V 2009 Synthesis of some coumarinyl chalcones of pharmacological interest Asian J. Chem. 21 5918Google Scholar
  25. 25.
    Wayne P A 2000 National committee for Clinical Laboratory Standards. Methods for dilution anti-microbial susceptibility tests for bacterial that grow aerobically: approved standard. NCCLS document M7-A5Google Scholar
  26. 26.
    Wayne P A 2002 National committee for Clinical Laboratory Standards. Reference method for broth dilution anti-fungal susceptibility testing of yeasts: Approved Standard. NCCLS document M27-A2Google Scholar
  27. 27.
    Wayne P A 2002 National committee for Clinical Laboratory Standards. Reference method for broth dilution anti-fungal susceptibility testing of filamentous fungi: Approved Standard. NCCLS document M38-AGoogle Scholar

Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  • Rajni Khajuria
    • 1
    • 2
  • Sheena Mahajan
    • 1
  • Ambica
    • 3
  • Kamal K Kapoor
    • 1
  1. 1.Department of ChemistryUniversity of JammuJammuIndia
  2. 2.Department of Chemistry and Chemical SciencesCentral University of JammuJammuIndia
  3. 3.Department of ChemistryGovernment Degree CollegeKathuaIndia

Personalised recommendations