Skip to main content

Advertisement

SpringerLink
Log in

One-pot three-component reaction for facile and efficient green synthesis of chromene pyrimidine-2,4-dione derivatives and evaluation of their anti-bacterial activity

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A facile and highly efficient one-pot three-component synthesis of chromene pyrimidine-2,4-dione derivatives from available substrates catalyzed by heteropoly acid (H3PW12O40) is described. In this protocol, the reaction of diverse aldehydes, 4-hydroxycoumarin, and 4-amino-1,3-dimethyluracil in the mixture of EtOH / H2O (1:2) at room temperature in the presence of heteropoly acid (H3PW12O40) as a highly efficient catalyst affords the corresponding chromene pyrimidine-2,4-dione in good to excellent yields. Operational simplicity, low cost, eco-friendly with the environment, easy workup and purification, short reaction time, high yield of products, green media of the reaction and mild conditions are the advantages of this method. The in vitro antibacterial activities of title compounds were obtained against Escherichia coli (ATTC 35218) and Staphylococcus aureus (ATCC 6538) as Gram-negative and Gram-positive bacteria, respectively, and their activities were compared to gentamycin and penicillin as reference drugs.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Okuhara T, Noritaka M, Makoto M (1996) Catalytic chemistry of heteropoly compounds. Advances in catalysis. Academic Press, London, p 113

    Google Scholar 

  2. Mizuno N, Misono M (1997) CurrOpin Solid State Mater Sci 2:84

    Article  CAS  Google Scholar 

  3. Dömling A (2002) Curr Opin Chem Biol 6:306

    Article  Google Scholar 

  4. Weber L (2002) Curr Med Chem 9:2085

    Article  CAS  Google Scholar 

  5. Zarenezhad E, Rad MN, Mosslemin MH, Tabatabaee M, Behrouz S (2014) J Chem Res 38:607

    Article  CAS  Google Scholar 

  6. Gourdeau H, Leblond L, Hamelin B, Desputeau C, Dong K, Kianicka I, Custeau D, Boudreau C, Geerts L, Cai SX, Drewe J (2004) Mol Cancer Ther 3:1375

    CAS  PubMed  Google Scholar 

  7. Cheng JF, Ishikawa A, Ono Y, Arrhenius T, Nadzan A (2003) Bioorg Med Chem Lett 13:3647

    Article  CAS  Google Scholar 

  8. Sangani CB, Shah NM, Patel MP, Patel RG (2012) J Serbian Chem Soc 77:1165

    Article  CAS  Google Scholar 

  9. Thomas N, Zachariah SM (2013) Asian J Pharm Clin Res 6:11

    CAS  Google Scholar 

  10. Pasunooti KK, Chai H, Jensen CN, Gorityala BK, Wang S, Liu XW (2011) Tetrahedron Lett 52:80

    Article  CAS  Google Scholar 

  11. Dansena HA, Dhongade HJ, Chandrakar K (2015) Asian J Pharm Clin Res 8:171

    CAS  Google Scholar 

  12. Rad MN, Behrouz S, Zarenezhad E, Kaviani N (2015) J Iran Chem Soc 12:1603

    Article  CAS  Google Scholar 

  13. Gleckman R, Blagg N, Joubert DW (1981) J Human Pharmacol Drug Ther 1:14

    Article  CAS  Google Scholar 

  14. Song H, Shin HS, Park KI (1998) Acta Crystallogr Sect C 54:1915

    Article  Google Scholar 

  15. Radha S, Mothilal KK, Thamaraichelvan A, Elangovana A (2016) J Chem Pharm Res 8:202

    CAS  Google Scholar 

  16. Kaur R, Kaur P, Sharma S, Singh G, Mehndiratta S, Bedi P, Nepali K (2015) Recent Pat Anti-Cancer Drug Discov 10:23

    Article  CAS  Google Scholar 

  17. Parker WB (2009) Chem Rev 109:2880

    Article  CAS  Google Scholar 

  18. Zhi C, Long ZY, Gambino J, Xu WC, Brown NC, Barnes M, Butler M, LaMarr W, Wright GE (2003) J Med Chem 46:2731

    Article  CAS  Google Scholar 

  19. Tucci FC, Zhu YF, Struthers RS, Guo Z, Gross TD, Rowbottom MW, Acevedo O, Gao Y, Saunders J, Xie Q, Reinhart GJ (2005) J Med Chem 48:1169

    Article  CAS  Google Scholar 

  20. Afsarian MH, Farjam M, Zarenezhad E, Behrouz S, Rad MN (2019) Acta ChimSlov 66:874

    CAS  Google Scholar 

  21. Zarenezhad E, Mosslemin MH, Alborzi A, Anaraki-Ardakani H, Shams N, Khoshnood MM, Zarenezhad A (2014) J Chem Res 38:337

    Article  CAS  Google Scholar 

  22. Rad MN, Behrouz S, Zarenezhad E, Moslemin MH, Zarenezhad A, Mardkhoshnood M, Behrouz M, Rostami S (2014) Med Chem Res 23:3810

    Article  Google Scholar 

  23. Abdolmohammadi A, Balalaie S, Barari M, Rominger F (2013) Comb Chem High Throughput Screen 16:150

    CAS  PubMed  Google Scholar 

  24. Fakheri-Vayeghan S, Abdolmohammadi S, Kia-Kojoori R (2018) Z Naturforsch B 73:545

    Article  CAS  Google Scholar 

  25. Bharti R, Parvin T (2015) Synth Commun 45:1442

    Article  CAS  Google Scholar 

  26. Bharti R, Parvin T (2015) RSC Adv 5:66833

    Article  CAS  Google Scholar 

  27. Karami B, Eskandari K, Khodabakhshi S, Hoseini SJ, Hashemian F (2013) RSC Adv 3:23335

    Article  CAS  Google Scholar 

  28. Lu GP, Cai C (2014) J Heterocycl Chem 51:1595

    Article  CAS  Google Scholar 

  29. Mosslemin MH, Zarenezhad E, Shams N, Rad MN, Anaraki-Ardakani H, Fayazipoor R (2014) J Chem Res 38:169

    Article  CAS  Google Scholar 

  30. Shams N, Mosslemin MH, Anaraki-Ardakani H, Zarenezhad E (2015) J Chem Res 39:270

    Article  CAS  Google Scholar 

  31. Khalafi-Nezhad A, Panahi F, Mohammadi S, Foroughi HO (2013) J Iran Chem Soc 10:189

    Article  CAS  Google Scholar 

  32. Jay JM, Loessner MJ, Golden DA (2008) Modern food microbiology. Springer Science and Business Media, Berlin

    Google Scholar 

Download references

Acknowledgements

We would like to offer our special thanks to Islamic Azd University Fasa branch for partial support of this research work.

Author information

Authors and Affiliations

  1. Department of Science, Fasa Branch, Islamic Azad University, P. O. Box: No. 364, Fasa, Fars, 7461713591, Iran

    Habib Ollah Foroughi & Mansoureh Kargar

  2. Department of Food Science and Technology, Fasa Branch, Islamic Azad University, P. O. Box: No. 364, Fasa, Fars, 7461713591, Iran

    Zahra Erjaee

  3. Noncommunicable Diseases Research Center, School of Medicine, Fasa University of Medical Sciences, Fasa, Iran

    Elham Zarenezhad

Authors
  1. Habib Ollah Foroughi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mansoureh Kargar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zahra Erjaee
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Elham Zarenezhad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Habib Ollah Foroughi.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 259 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Foroughi, H.O., Kargar, M., Erjaee, Z. et al. One-pot three-component reaction for facile and efficient green synthesis of chromene pyrimidine-2,4-dione derivatives and evaluation of their anti-bacterial activity. Monatsh Chem 151, 1603–1608 (2020). https://doi.org/10.1007/s00706-020-02692-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-020-02692-5

Keywords

Search

Navigation