Chemistry of Heterocyclic Compounds

, Volume 52, Issue 3, pp 172–176 | Cite as

Microwave-assisted one-pot synthesis of some new flavonols by modified Algar–Flynn–Oyamada reaction and their antimicrobial activity

  • Dongamanti Ashok
  • Mohsin Ahmed Kifah
  • Bommidi Vijaya Lakshmi
  • Madderla Sarasija
  • Shaik Adam

A new series of 3-hydroxy-2-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]-4H-chromen-4-ones has been synthesized from substituted 2-hydroxyacetophenones and 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde using NaOH and H2O2 by modified Algar–Flynn–Oyamada reaction under conventional and microwave irradiation conditions. In this method flavonols are synthesized without isolating chalcones in good yields (80–85%). The structures of the compounds were established on the basis of IR, 1H, 13C NMR and mass spectral and elemental analysis data. The synthesized compounds were screened for their antibacterial and antifungal activities.


3-hydroxy-2-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]-4H-chromen-4-ones 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde antimicrobial activity microwave irradiation modified Algar–Flynn–Oyamada reaction 


Supplementary material

10593_2016_1852_MOESM1_ESM.pdf (2.3 mb)
ESM 1 (PDF 2395 kb)


  1. 1.
    Primo, F. T.; Fröhlich, P. E. Acta Farm. Bonaerense 2005, 24, 421.Google Scholar
  2. 2.
    Riedel, R. Arzneim. Forsch. 1981, 31, 655.Google Scholar
  3. 3.
    Kumar, V.; Kaur, K.; Gupta, G. K.; Sharma, A. K. Eur. J. Med. Chem. 2013, 69, 735.CrossRefGoogle Scholar
  4. 4.
    Nargund, L. V. G.; Hariprasad, V.; Reddy, G. R. N. Indian J. Pharm. Sci. 1993, 55, 1.Google Scholar
  5. 5.
    Sangani, C. B.; Makawana, J. A.; Zhang, X.; Teraiya, S. B.; Lin, L.; Zhu, H.-L. Eur. J. Med. Chem. 2014, 76, 549.CrossRefGoogle Scholar
  6. 6.
    Sankappa Rai, U.; Isloor, A. M.; Shetty, P.; Pai, K. S. R.; Fun, H. K. Arabian J. Chem. 2015, 8, 317.CrossRefGoogle Scholar
  7. 7.
    Blair, B.; Fatheree, R. P.; Fleury, M.; Gendron, R.; Hudson, R.; McKinnell, R. M.; Wilson, M. WO Patent 2011005674.Google Scholar
  8. 8.
    Secci, D.; Bolasco, A.; Chimenti, P.; Carradori, S. Curr. Med. Chem. 2011, 18, 5114.CrossRefGoogle Scholar
  9. 9.
    Xu, L.; Zhang, X.; Li, X.; Wang, M.; Yuan, B. CN Patent 103232432.Google Scholar
  10. 10.
    Dong, F.; Chen, X.; Liu, X.; Xu, J.; Li, Y.; Shan, W.; Zheng, Y. J. Chromatogr. A 2012, 1262, 98.CrossRefGoogle Scholar
  11. 11.
    Amr, A.-G.; Abdel-Latif, N. A.; Abdalla, M. M. Acta Pharm. 2006, 56, 203.Google Scholar
  12. 12.
    Oh, H. C.; Cho, J. H.; El-Gamal, M. KR Patent 2013010514.Google Scholar
  13. 13.
    Lee, H. I.; Le Hir de Fallois, L. P.; Timmons, P. R.; Cawthorne, W. G.; De Leon, A. P. WO Patent 2008005489.Google Scholar
  14. 14.
    Sherman, T. D.; Duke, M. V.; Clark, R. D.; Sanders, E. F.; Matsumoto, H.; Duke, O. S. Pestic. Biochem. Physiol. 1991, 40, 236.CrossRefGoogle Scholar
  15. 15.
    Ragab, F. A.; Abdel Gawad, N. M.; Georgey, H. H.; Said, M. F. Eur. J. Med. Chem. 2013, 63, 645.CrossRefGoogle Scholar
  16. 16.
    Mohy El-Din, M. M; Senbel, A. M.; Bistawroos, A. A.; El-Mallah, A.; Nour El-Din, N. A.; Bekhit, A. A.; Abd El Razik, H. A. Basic Clin. Pharmacol. Toxicol. 2011, 108, 263.CrossRefGoogle Scholar
  17. 17.
    Hantoon, M. A. Minn. Med. 2001, 84, 102.Google Scholar
  18. 18.
    Zhang, X.; Li, X.; Allan, G. F.; Sbriscia, T.; Linton, O.; Lundeen, S. G.; Sui, Z. J. Med. Chem. 2007, 50, 3857.CrossRefGoogle Scholar
  19. 19.
    Yang, X.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. RSC Adv. 2012, 2, 11061.CrossRefGoogle Scholar
  20. 20.
    Fong, T. M.; Heymsfield, S. B. Int. J. Obes. 2009, 33, 947.CrossRefGoogle Scholar
  21. 21.
    Rademacher, P. M.; Woods, C. M.; Huang, Q.; Szklarz, G. D.; Nelson, S. D. Chem. Res. Toxicol. 2012, 25, 895.CrossRefGoogle Scholar
  22. 22.
    Bhuiyan, M. H.; Khandkar, M. M. Pak. J. Sci. Ind. Res. 2009, 52, 180.Google Scholar
  23. 23.
    Murray, M. T. Encyclopedia of Nutritional Supplements; Random House: New York, 1996, p. 320.Google Scholar
  24. 24.
    Cimanga, K.; Ying, L.; De Bruyne, T.; Apers, S.; Cos, P.; Hermans, N.; Bakana, P.; Tona, L.; Kambu, K.; Kalenda, D. T.; Pieters, L.; Vanden Berghe, D.; Vlietinck, A. J. J. Pharm. Pharmacol. 2001, 53, 757.CrossRefGoogle Scholar
  25. 25.
    Bandgar, B. P.; Patil, S. A.; Korbad, B. L.; Biradar, S. C.; Nile, S. N.; Khobragade, C. N. Eur. J. Med. Chem. 2010, 45, 3223.CrossRefGoogle Scholar
  26. 26.
    Ercelen, S.; Klymchenko, A. S.; Demchenko, A. P. Anal. Chim. Acta 2002, 464, 273.CrossRefGoogle Scholar
  27. 27.
    Klymchenko, A. S.; Avilov, S. V.; Demchenko, A. P. Anal. Biochem. 2004, 329, 43.CrossRefGoogle Scholar
  28. 28.
    Franke, A. A.; Cooney, R. V.; Custer, L. J.; Mordan, L. J.; Tanaka, Y. Adv. Exp. Med. Biol. 1998, 439, 237.CrossRefGoogle Scholar
  29. 29.
    Zwergel, C.; Valente, S.; Salvato, A.; Xu, Z.; Talhi, O.; Mai, A.; Silva, A.; Altucci, L.; Kirsch, G. Med. Chem. Commun. 2013, 4, 1571.CrossRefGoogle Scholar
  30. 30.
    Chohan, Z. H.; Rauf, A.; Naseer, M. M.; Somra, M. A.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2006, 21, 173.CrossRefGoogle Scholar
  31. 31.
    Kumar, S.; Pandey, A. K. Sci. World J. 2013, 29, 162750.Google Scholar
  32. 32.
    Jain, A. C.; Gupta, S. M.; Sharma, A. Bull. Chem. Soc. Jpn. 1983, 56, 1267.CrossRefGoogle Scholar
  33. 33.
    Girish, D. H.; Ashish, P. K.; Atish, H. R.; Rajesh, H. T.; Satish, S. B.; Mahendra, J. P.; Vandana, M. K. Med. Chem. Res. 2014, 23, 461.CrossRefGoogle Scholar
  34. 34.
    Ashok, D.; Vijaya Lakshmi, B.; Ravi, S.; Ganesh, A. Med. Chem. Res. 2015, 24, 1487.CrossRefGoogle Scholar
  35. 35.
    Serdiuk, I. E.; Roshal, A. D.; Błażejowski, J. Chem. Heterocycl. Compd. 2014, 50, 396. [Khim. Geterotsikl. Soedin. 2014, 431.]Google Scholar
  36. 36.
    Ashok, D.; Ravi, S.; Vijaya Lakshmi, B.; Ganesh, A. J. Serb. Chem. Soc. 2015, 80, 305.CrossRefGoogle Scholar
  37. 37.
    Kiyani, H.; Albooyeh, F.; Fallahnezhad, S. J. Mol. Struct. 2015, 1091, 163.CrossRefGoogle Scholar
  38. 38.
    Saha, K.; Mukherjee Pulok, K.; Mandal, S. C.; Pal, M.; Saha, B. P. Indian Drugs 1995, 32, 402.Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Dongamanti Ashok
    • 1
  • Mohsin Ahmed Kifah
    • 1
  • Bommidi Vijaya Lakshmi
    • 1
  • Madderla Sarasija
    • 2
  • Shaik Adam
    • 3
  1. 1.Department of ChemistryOsmania UniversityHyderabadIndia
  2. 2.Department of ChemistrySatavahana UniversityKarimnagarIndia
  3. 3.Regional Agricultural Research StationANGRAUTirupatiIndia

Personalised recommendations