Advertisement

Microwave-assisted synthesis, molecular docking, and biological evaluation of 2-arylidene-2H-furo[2,3-f]chromen-3(7H)-ones as antioxidant and antimicrobial agents

  • 168 Accesses

  • 2 Citations

Abstract

An efficient microwave-assisted method of synthesis of some novel 2-arylidene-2H-furo[2,3-f]chromen-3(7H)-ones 6a–j in excellent yields was described and structural assignment of the products was confirmed on the basis of IR, 1H NMR, 13C NMR, MS, and analytical data. The synthesized compounds were screened for antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl and hydrogen peroxide radicals. The compounds 5d, 5h, 6a, 6e, and 6j exhibited better radical scavenging ability. Antimicrobial activity results demonstrated that compounds 5b, 5e, 6b, 6c, and 6e showed promising antimicrobial potency. The in silico molecular docking studies were also carried out for the inhibition of cyclooxygenase-II enzyme. These molecular docking results were well complemented to the antioxidant activity studies.

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

Access options

Buy single article

Instant unlimited access to the full article PDF.

US$ 39.95

Price includes VAT for USA

Subscribe to journal

Immediate online access to all issues from 2019. Subscription will auto renew annually.

US$ 99

This is the net price. Taxes to be calculated in checkout.

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3

References

  1. Ashok D, Rangu K, Rao VH, Gundu S, Srilata B, Vijjulatha M (2016) Microwave-assisted synthesis, molecular docking and antimicrobial activity of novel 2-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones. Med Chem Res 25:501–514

  2. Azoro C (2002) Antibacterial activity of crude aqueous of Azadrichta indica on Salmonella typhi. World J Biotechnol 3:347–351

  3. Bishnu J, Sunil L, Anuja S (2009) Antibacterial property of different medicinal plants: Ocimum sanctum, Cinnamomum zeylanicum, Xanthoxylum armatum and Origanum majorana. J Sci Eng Technol 5:143–150

  4. Boumendjel A (2003) Aurones: a subclass of flavones with promising biological potential. Curr Med Chem 10:2621–2630

  5. Burits M, Bucar F (2000) Antioxidant activity of Nigella sativa essential oil. Phytother Res 14:323–328

  6. Cheng H, Zhang L, Liu Y, Chen S, Cheng H, Lu X, Zheng Z, Zhou GC (2010) Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines. Eur J Med Chem 45:5950–5957

  7. Chung KT, Thomasson WR, Wu-Yuan CD (1990) Growth inhibition of selected food-borne bacteria, particularly Listeria monocytogenes, by plant extracts. J Appl Bacteriol 69:498–503

  8. Cuendet M, Hostettmann K, Potterat O, Dyatmiko W (1997) Iridoid glucosides with free radical scavenging properties from Fagraea blumei. Helv Chim Acta 80:1144–1152

  9. Detsi A, Majdalani M, Kontogiorgis CA, Hadjipavlou-Litina D, Kefalas P (2009) Natural and synthetic 2′-hydroxy-chalcones and aurones. Bioorg Med Chem 17:8073–8085

  10. Gulcin I, Buyukokuroglu ME, Oktay M, Kufrevioglu OI (2003) Antioxidant and analgesic activities of turpentine of Pinus nigra Arn. subsp. pallsiana (Lamb.) Holmboe. J Ethnopharmacol 86:51–58

  11. Hangum-balkir Y, Mckenney ML (2012) Determination of antioxidant activities of berries and Resveratrol. Green Chem Lett Rev 5:147–153

  12. Janovska D, Kubikova K, Kokoska L (2003) Screening for antimicrobial activity of some medicinal plants species of traditional Chinese medicine. J Food Sci 21:107–110

  13. Jung MJ, Chung HY, Kang SS, Choi JH, Bae KS, Choi JS (2003) Antioxidant activity from the stem bark of Albizzia julibrissin. Arch Pharm Res 6:458–462

  14. Kalgutkar AS, Crews BC, Rowlinson SW, Garner C, Seibert K, Marnett LJ (1998) Aspirin-like molecules that covalently inactivate cyclooxygenase-2. Science 280:1268–1270

  15. Kerboeuf D, Riou M, Guégnard F (2008) Flavonoids and related compounds in parasitic disease control. Mini Rev Med Chem 8:116–28

  16. Kim IT, Park YM, Shin KM, Ha JH, Choi JW, Jung HJ, Park HJ, Lee KT (2004) Anti-inflammatory and anti-nociceptive effects of the extract from Kalopanax pictus, Pueraria thunbergiana and Rhus verniciflua. J Ethnopharmacol 94:165–173

  17. Ku CS, Mun SP (2008) Characterization of seed oils from fresh Bokbunja (Rubus coreanus Miq.) and wine processing waste. Bioresour Technol 99:2852–2856

  18. Lee EH, Song DG, Lee JY, Pan CH, Um BH, Jung SH (2008) Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biol Pharm Bull 31:1626–1630

  19. Pare PW, Dmitrieva N, Mabry TJ (1991) Phytoalexin aurone induced in Cephalocereus senilis liquid suspension culture. Phytochemistry 30:1133–1135

  20. Park KY, Jung GO, Lee KT, Choi JW, Choi MY, Kim GT, Jung HJ, Park HJ (2004) Antimutagenic activity of flavonoids from the heartwood of Rhus verniciflua. J Ethnopharmacol 90:73–79

  21. Politeo O, Jukic M, Milos M (2007) Chemical composition and antioxidant capacity of free volatile aglycones from basil (Ocimum basilicum L.) compared with its essential oil. Food Chem 101:379–385

  22. Roussaki M, Lima SC, Kypreou AM, Kefalas P, Cordeiro da Silva A, Detsi A (2012) Aurones: a promising heterocyclic scaffold for the development of potent antileishmanial agents. Int J Med Chem 196921, doi:10.1155/2012/196921

  23. Ruch RJ, Cheng SJ, Klaunig JE (1989) Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis 10:1003–1008

  24. Schoepfer J, Fretz H, Chaudhuri B, Muller L, Seeber E, Meijer L, Lozach O, Vangrevelinghe E, Furet P (2002) Structure-based design and synthesis of 2-benzylidene-benzofuran-3-ones as flavopiridol mimics. J Med Chem 45:1741–1747

  25. Shrestha S, Natarajan S, Park JH, Lee DY, Cho JG, Kim GS, Jeon YJ, Yeon SW, Yang DC, Baek NI (2013) Potential neuroprotective flavonoid-based inhibitors of CDK5/p25 from Rhus parviflora. Bioorg Med Chem Lett 23:5150–5154

  26. Sim HM, Loh KY, Yeo WK, Lee CY, Go ML (2011) Aurones as modulators of ABCG2 and ABCB1. Chem Med Chem 6:713–724

  27. Song MY, Jeong GS, Kwon KB, Ka SO, Jang HY, Park JW, Kim YC, Park BH (2010) Sulfuretin protects against cytokine-induced beta-cell damage and prevents streptozotocin-induced diabetes. Exp Mol Med 42:628–638

  28. Sreenivas P (2011) Synthesis and antibacterial activity of some new spiro[pyrano[2,3-f]chromene-2,10-cycloalkan]-4-ones and 10-alkylspiro[pyrano[2,3-f]chromene-2,40-piperidin]-4-ones. Indian J Chem Sect B 50B:1484–1490

  29. Tepe B, Daferera D, Sokmen A, Sokmen M, Polissiou M (2005) Antimicrobial and antioxidant activities of the essential oil and various extracts of Salvia tomentosa Miller (Lamiaceae). Food Chem 90:333–340

  30. Turkoglu A, Duru ME, Mercan N, Kivrak I, Gezer K (2007) Antioxidant and antimicrobial activities of laetiporus sulphurus (bull.) Murrill. Food Chem 101:267–273

  31. Venkateswarlu S, Panchagnula GK, Gottumukkala AL, Subbaraju GV (2007) Synthesis, structural revision, and biological activities of 4′-chloroaurone, a metabolite of marine brown alga Spatoglossum variabile. Tetrahedron 63:6909–6914

  32. Yin H, Xu L, Porter NA (2011) Free radical lipid peroxidation: mechanisms and analysis. Chem Rev 111:5944–5972

Download references

Acknowledgements

The authors are grateful to Department of Chemistry, Osmania University for providing laboratory facilities, CFRD, and spectral analysis. One of the authors, K.R. is thankful to UGC-New Delhi, India, for granting Senior Research Fellowship.

Author information

Correspondence to Dongamanti Ashok.

Ethics declarations

Conflict of interest

The authors declare that they have no competing interests.

Electronic supplementary material

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Ashok, D., Rangu, K., Gundu, S. et al. Microwave-assisted synthesis, molecular docking, and biological evaluation of 2-arylidene-2H-furo[2,3-f]chromen-3(7H)-ones as antioxidant and antimicrobial agents. Med Chem Res 26, 1735–1746 (2017). https://doi.org/10.1007/s00044-017-1834-9

Download citation

Keywords

  • Chromenone
  • Aurone
  • Microwave irradiation
  • Molecular docking
  • Antioxidant
  • Antimicrobial