SYNTHESIS OF FLAVONES FROM 2-HYDROXY ACETOPHENONE AND AROMATIC ALDEHYDE DERIVATIVES BY CONVENTIONAL METHODS AND GREEN CHEMISTRY APPROACH
Objective: Flavones occupy a special place in the realm of natural and synthetic organic chemistry owing to their diversified biological activities. In this study, a series of chalcone derivatives were synthesized and after cyclization of chalcone to synthesized various substituted flavone derivatives (2A-2L).Â
Methods: The reaction of 2-hydroxy acetophenone with substituted aromatic aldehydes produced chalcone by trituration (NaOH) and conventional methods (KOH/EtOH), which upon further cyclization with dimethyl sulfoxide/I Â resulted to form flavone derivatives.
Results: The purity of compounds was ascertained by melting point and thin-layer chromatography. The synthesized compounds have been characterized by mass, infrared, and1H nuclear magnetic resonance spectral analysis.
Conclusion: Based on spectral data, it was proved that all synthesized chalcones and flavones derivatives meet the standard values of various spectral techniques and further it will be evaluated for pharmacological activities.
Keywords: Chalcone, Flavone, Trituration, Conventional, Claisen-Schmidt condensation.
2. Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry 2000; 55:481â€“504. (URL: https://www.ncbi.nlm.nih.gov/pubmed/11130659)
3. Pal D, Verma P. Flavonoids: a powerful and abundant source of antioxidants. Inter J of Pharm and Pharmaceutical Sci 2013;5(3): 95-98.(URL: http://www.ijppsjournal.com/Vol5Issue3/7048.pdf)
4. Riceâ€Evans CA, Miller NJ, Paganga G, Structureâ€antioxidant activity relationships of flavonoids and phenolic acids. Free Rad Biol Med 1996; 20(7): 933â€56. (URL: https://www.ncbi.nlm.nih.gov/pubmed/8743980)
5. Riceâ€Evans C, Flavonoids antioxidants. Curr Med Chem 2001; 8(7): 797â€807. (URL: https://www.ncbi.nlm.nih.gov/pubmed/11375750)
6. Pietta PG, Flavonoids as antioxidants. J Nat Prod 2000; 63(7): 1035â€42.(URL: https://www.ncbi.nlm.nih.gov/pubmed/10924197)
7. Chan ECH, Patchareewan P, Owen LW. Relaxation to flavones and flavonols in rat isolated thoracic aorta: Mechanism of action and structure activity relationships. J Cardiovasc Pharmacol 2000; 35(2): 326â€33.(URL: https://www.ncbi.nlm.nih.gov/pubmed/10672869)
8. Almeida ER, Xavier HS, Chaves TM, Couto GBC, Aragaoâ€Neto AC, Silva AR, Da Silva LLS Anxiolytic and anticonvulsant effect of dioclenol flavonoids isolated from stem bark of Dioclea grandiflora on mice. Inter J of App Res and Nat Pro. 2009â€10; 2(4): 44â€51.(URL: http://www.ijarnp.org/index.php/ijarnp/article/view/40)
9. Liu YL, Ho DK, Cassady JM, Cook VM , Barid WM. Isolation of potential cancer chemo preventive agents from Eriodictyon californicum. J Nat Prod 1992; 55(3): 357â€63.(URL: https://www.ncbi.nlm.nih.gov/pubmed/1593282)
10. Ramos, S. Effects of dietary flavonoids on apoptic pathways related to cancer chemoprevention. J of Nut Biochem2007; 18: 427-42.(URL: https://www.ncbi.nlm.nih.gov/pubmed/17321735)
11. Ren W, Qiao Z, Wang H, Zhu L, Zhang Li. Flavonoids: Promising Anticancer Agents. Med Res Rev, 2003; 23(4): 519-34. (URL: https://www.ncbi.nlm.nih.gov/pubmed/12710022)
12. Shin JS, Kim KS, Kim MB, Jeong JH, Kim BK. Synthesis and hypoglycemic effect of chrysin derivatives. Bioorg Med Chem Lett 1999; 9(6): 869â€74.(URL: https://www.ncbi.nlm.nih.gov/pubmed/10206552)
13. Dao TT, Chi YS, Kim J. Kim HP, Kim S, Park H. Synthesis and inhibitory activity against COXâ€2 catalyzed prostaglandin production of chrysin derivatives. Bioorg Med Chem Lett 2004; 14(5): 1165â€67.(URL: https://www.ncbi.nlm.nih.gov/pubmed/14980657)
14. Theja DN, Choudary TP, Reddy MI, Gupta A,Reddy KU.A facile synthesis of flavone derivatives used as potent anti-inflammatory agents. Inter J of Pharm and Pharmaceutical Sci 2011; 3(2): 51-54. (URL: http://www.ijppsjournal.com/Vol3Suppl2/970.pdf)
15. Mostahar S, Alam S, Islam A.Cytotoxic and antimicrobial activities of some synthetic flavones. Indian J Chem 2006; 45B: 1478â€86.(URL: http://nopr.niscair.res.in/handle/123456789/6487)
16. Tapas AR, Sakarkar DM, Kakde RB. Flavonoids as nutraceuticals: A Review. Trop J of Pharm Res 2008; 7: 1089-99. (URL: http://www.bioline.org.br/pdf?pr08030)
17. Kakati D, Sarma JC. Microwave assisted solvent free synthesis of 1,3diphenylpropenones. Chem Cent J 2011; 5:8:1-5. (URL: https://ccj.springeropen.com/articles/10.1186/1752-153X-5-8)
18. Sashidhara KV, Rosaiah JN, Kumar A. Iodinecatalyse mild and efficient method for the synthesis of chalcones. Synthetic Communication 2009; 39(3): 2288-96. (URL: http://www.tandfonline.com/doi/abs/10.1080/00397910802654724?journalCode=lsyc20)
19. Li JT , Yang WZ , Wang SX, Li SH and Li SH. Improved synthesis of chalcones under ultrasound irradiation. Ultra Sonochem 2002; 9(5): 237-39. (URL: http://www.sciencedirect.com/science/article/pii/S1350417702000792)
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.