Alumina-K3PO4 Solid Supported Microwave Synthesis of 1, 3-diaryl-2- propene-1-one Derivatives as a Prominent Antioxidant Scavenger

Author(s): Pravinkumar Patil, Gangadhar Bhopalkar, Sainath Zangade*

Journal Name: Current Microwave Chemistry

Volume 7 , Issue 2 , 2020

Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Background: The various industrial processes have a diverse effect on the environment through pollution. In view of these observations, some environmentally benign synthetically protocols have developed under green chemistry. For rapid and sustainable synthesis, the microwave irradiation (MI) has gained popularity as a powerful tool compared to conventional synthesis. The present study describes the synthesis of novel substituted 1, 3-diaryl-2-propene-1-one derivative using alumina supported K3PO4-MWI combination.

Objective: Chalcones are important compounds which are widely spread in nature like in fruits, vegetables, tea, spices, etc. The 2’-hydroxy derivative of chalcones plays an important role in the synthesis of bioactive compounds. The present communication deals with a convenient and rapid synthesis of 1, 3-diaryl-2-propene-1-one under the support of alumina-tripotassium phosphate and microwave irradiation. Our efforts are focused on the introduction of typical and easier route for the synthesis of title compounds using a microwave. All synthesized chalcones have been screened and evaluated for the antioxidant activity by DPPH and nitric oxide radical scavenging. Some of these compounds are found to be more potent scavengers and may lead to the development of a new class of antioxidants.

Methods: The α, β-unsaturated carbonyl functionality contains two electrophilic centers allowing them to undergo addition and cyclization reactions with different nucleophiles. In the literature survey, we found that Chalcones were synthesized using tripotassium phosphate catalyst under refluxing by a conventional method. A novel method for the synthesis of 1, 3-diaryl-2-propene-1-one via Claisen Schmidt has been introduced by reacting substituted 2’- hydroxyl acetonaphthones with substituted aromatic aldehydes under the support of basic alumina –tripotassium phosphate via microwave radiations. Formation of corresponding Chalcones was confirmed by spectral studies followed by their screening for antioxidant activity. The scavenging activity is expressed in terms of % inhibition and IC50 value (μg/ml).

Results: The structures of newly synthesized Chalcones were confirmed and in good agreement with obtained spectral analysis such as IR, NMR, Mass and elemental analysis. Commercially available basic alumina and tripotassium phosphate in combination of microwave were utilized and found to be effective, convenient route for the synthesis of 1, 3-diaryl-2-propene-1-one derivatives with desirable yields in short reaction time (5-12 min). The results of antioxidant activity revealed that the IC50 value for compounds 3a, 3d, 3e, 3f, 3g, 3h, 3j, 3l and 3n are lower than that of standard ascorbic acid to scavenge DPPH radical. This indicates that these compounds are more significant scavengers in comparison with standard drug. On the other hand, compounds 3a, 3b, 3c, 3d, 3g, 3l and 3n are more potent scavengers for NO free radical.

Conclusion: We have introduced an efficient, ecofriendly, simple and fast microwave assisted method using basic alumina-tripotassium phosphate for the synthesis of 1, 3-diaryl-2-propene-1- one derivatives. Microwave irradiation provides an effective way for the preparation of Chalcones in terms of several advantages as a simple procedure, short reaction time, milder reaction condition, cleaner reaction and excellent yield. The scavenging activity of chalcones against DPPH and NO free radicals showed excellent properties of antioxidants.

Keywords: 2-hydroxy acetonaphthones, aldehydes, alumina-tripotassium phosphate, Microwave, 1, 3-diaryl-2-propene-1-one, Antioxidant activity.

Sarada, S.R.; Jadhav, W.N.; Bhusare, S.R.; Wasmatkar, S.K.; Dake, S.A.; Pawar, R.P. Solvent-freeNaOH-Al2O3 supported synthesis of 1,3-diaryl-2-propene-1-ones. Inter. J. Chem. Tech. Res., 2009, 1, 265-269.
Asiri, A.M.; Khan, S.A. Synthesis and anti-bacterial activities of a bis-chalcone derived from thiophene and its bis-cyclized products. Molecules, 2011, 16(1), 523-531.
[] [PMID: 21228758]
Kakati, D.; Sarma, J.C. Microwave assisted solvent free synthesis of 1,3-diphenylpropenones. Chem. Cent. J., 2011, 5, 8.
[] [PMID: 21329529]
Biradar, J.S.; Sasidhar, B.S.; Parveen, R. Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. Eur. J. Med. Chem., 2010, 45(9), 4074-4078.
[] [PMID: 20594623]
Nowakowska, Z. A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med. Chem., 2007, 42(2), 125-137.
[] [PMID: 17112640]
Kumar, D.; Kumar, N.M.; Akamatsu, K.; Kusaka, E.; Harada, H.; Ito, T. Synthesis and biological evaluation of indolyl chalcones as antitumor agents. Bioorg. Med. Chem. Lett., 2010, 20(13), 3916-3919.
[] [PMID: 20627724]
Ducki, S.; Forrest, R.; Hadfield, J.A.; Kendall, A.; Lawrence, N.J.; McGown, A.T.; Rennison, D. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg. Med. Chem. Lett., 1998, 8(9), 1051-1056.
[] [PMID: 9871706]
Husain, A.; Rashid, M.; Mishra, R.; Kumar, D. Bis-chalcones and flavones: synthesis and antimicrobial activity. Acta Pol. Pharm., 2013, 70(3), 443-449.
[PMID: 23757935]
Miranda, C.L.; Stevens, J.F.; Ivanov, V.; McCall, M.; Frei, B.; Deinzer, M.L.; Buhler, D.R. Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro. J. Agric. Food Chem., 2000, 48(9), 3876-3884.
[] [PMID: 10995285]
Murakami, S.; Muramatsu, M.; Aihara, H.; Otomo, S. Inhibition of gastric H+,K(+)-ATPase by the anti-ulcer agent, sofalcone. Biochem. Pharmacol., 1991, 42(7), 1447-1451.
[] [PMID: 1656986]
Liu, M.; Wilairat, P.; Go, M.L. Antimalarial alkoxylated and hydroxylated chalcones [corrected]: structure-activity relationship analysis. J. Med. Chem., 2001, 44(25), 4443-4452.
[] [PMID: 11728189]
Piste, P. Synthesis of chalcones by grindstone chemistry as an intermediate in organic synthesis. I. J. Curr. Sci., 2014, 13, 62-66.
Sarojini, B.K.; Narayana, B.; Ashalatha, B.V.; Indira, J.; Lobo, K.G. Synthesis,crystal growth and studies on non-linear optical property of new chalcones. J. Cryst. Growth, 2006, 295, 54-59.
Shettigar, S.; Umesh, G.; Chandrasekharan, K.; Sarojin, B.K.; Narayana, B. Studies on third order nonlinear optical properties of chalcone derivatives in polymer host. Opt. Mater., 2008, 30, 1297-1303.
Delavaux-Nicot, B.; Maynadie, J.; Lavabre, D.; Fery-Forgues, S. Ca2+vs Ba2+ electrochemical detection by two disubstituted ferrocenyl chalcone chemosensors. Study of the ligand-metal interactions in CH3CN. J. Org. Chem., 2007, 692, 874-886.
Lu, Z.; Zhang, F.; Lei, X.; Yang, L.; Xu, S.; Duan, X. In situ growth of layered double hydroxide films on anodic aluminium oxide/aluminium and its catalytic feature in aldol condensation of acetone. Chem. Eng. Sci., 2008, 63, 4055-4062.
Ali, M.F.; Khlafulla, A.M. Friendly and efficient synthesis of chalcone derivatives under solvent free condition. Res. Rev. J. Pha., 2016, 6, 1-8.
Dev, S.; Dhaneshwar, S.R. A solvent-free protocol for the green synthesis of heterocyclic chalcones. Sch. Res. Lib., 2013, 5, 219-223.
Prasad, Y.R.; Rao, A.L.; Rambabu, R.; Ravikumar, P. Synthesis and biological evaluation of some novel chalcone derivatives. Orient. J. Chem., 2007, 23, 927-937.
Rao, M.S.; Kotesh, J.; Narukulla, R.; Duddeck, H. Synthesis and spectroscopic characterization of some chromo chalcones and their dihydro derivatives. ARKIVOC, 2004, XIV, 96-102.
Singh, J.; Dulawat, M.; Jaitawat, N.; Chundawat, S.; Devpura, A.; Dulawat, S. Microwave enhanced Claisen-Schmidt condensation: A green route to chalcones. Indian J. Chem., 2012, 51B, 1623-1627.
Shntaif, A.H. Green synthesis of chalcones under microwave irradiation. Int. J. Chemtech Res., 2016, 9, 36-39.
Petrov, V.; Ivanova, Y.; Gerova, M. SOCl2/EtOH: Catalytic system for synthesis of chalcones. Catal. Commun., 2008, 9, 315-317.
Macquarrie, D.; Nazih, R.; Sebti, S. KF/natural phosphate as as efficient catalyst for synthesis of 2′-hydrocychalcones and flavonones. Green Chem., 2002, 4, 56-59.
Pore, D.M.; Desai, U.V.; Thopate, T.S.; Wadgaonkar, P.P. Efficient synthesis of chalcones at room temperature in the presence of Potassium phosphate. Rus. J. Org. Chem., 2007, 43, 1088-1089.
Zhang, Z.; Dong, Y.W.; Guan, W.U.; Wang, G.W. Efficient and clean aldol condensation catalyzed by sodium carbonate in water. Chem. Lett., 2003, 32, 966-967.
Sebti, S.; Solhy, A.; Somabh, A.; Kossir, A.; Oamimoun, H. Dramatic activity enhancement of natural phosphate catalyst by lithium nitrate: An efficient synthesis of chalcones. Catal. Commun., 2002, 3, 335-339.
Thirunarayanan, G.; Vanangamudi, G. Synthesis of some 4-bromo-1-naphthyl chalcones using silica-sulfuric acid reagent under solvent free conditions. ARKIVOC, 2006, 12, 58-64.
Kateb, B.A.; Hussien, A.A.; Basser, M.A. Microwave-Assisted efficient synthesis of ortho hydroxyl chalcones as probes for biological activities. IJPPR, 2016, 6, 210-217.
Bhuiyan, M.M.H.; Hossain, M.I.; Mahmud, M.M.; Al-Amin, M. Microwave assisted efficient synthesis of chalcones as probes for antimicrobial activities. Chem. J., 2011, 01, 21-28.
Srivastava, Y.K. Ecofriendly microwave assisted synthesis of some chalcones. Ras. J. Chem., 2008, 4, 884-886.
Unchadkar, A.; Zangade, S.; Shinde, A.; Deshpande, M. Microwave assisted synthesis of some halo substituted chalcones. J. Tur. Che. Soc., 2015, 2, 1-8.
Calvino, V.; Picallo, M.; Lopez-peinado, A.; Martin-aranda, R.; Duran-valle, C. Ultrasound accelerated claisen-schimdt condensation: a green route to chalcones. Appl. Surf. Sci., 2006, 252, 6071-6074.
Zangade, S.; Mokale, S.; Vibhute, A.; Vibhute, Y. An efficient and operationally simple synthesis of some new chalcones by using grinding techinque. Chem. Sci. J., 2011, 13, 1-6.
Senthilkumar, G.; Neelkandan, K.; Mankandan, H. A convenient,green,solvent free synthesis and characterization of novel fluoro chalcones under grind-stone chemistry. Pel.Res.Lib., 2014, 5, 106-113.
Rateb, N.; Zohdi, H. Atom-efficient, solvent-free, green synthesis of chalcones by grinding. Synth. Commun., 2009, 39, 2789-2794.
Eddarir, S.; Catelle, N.; Bakkour, Y.; Ranlando, C. An efficient synthesis of chalcones based on the Suzuki reaction. Tetra.Lett., 2003, 44, 5359-5363.
Shivshankar, S.; Chavan, S.; Vibhute, Y. Solvent free synthesis of chalcones and antioxidant activity. J. Adv.Che.Sci., 2016, 2, 373-375.
Nanekar, V.; Shriram, V.; Khare, T.; Kumar, V. Nrf2/HO-1 Mediated antioxidant activities,cytotoxicity analysis and LC-ESI/MS Profiling of Eulophianuda L. Nat. Prod. J., 2019, 9, 1-11.
Ismail, S.M.; Leelavati, S. Evaluation of antioxidant activity of anisomelesmalabarica R Br and clerodendrumserratum L. extracts against rheumatism. RJPBCS, 2011, 4, 488-495.
Xiang, S.; Yang, P.; Guo, H.; Zhang, S.; Zhang, X.; Zhu, F.; Li, Y. Green tea makes polyphenol nanoparticles with radical-scavenging activities. Macromol. Rapid Commun., 2017, 38(23)1700446
[] [PMID: 28921705]
Wang, X.; Chen, Z.; Yang, P.; Hu, J.; Wang, Z.; Li, Y. Size control synthesis of melanin-like polydopamine nanoparticles by tuning radicals. Polym. Chem., 2019, 10, 4194-4200.
Yang, P.; Zhang, S.; Zhang, N.; Wang, Y.; Zhong, J.; Sun, X.; Qi, Y.; Chen, X.; Li, Z.; Li, Y. Tailoring synthetic melanin nanoparticles for enhanced photothermal therapy. ACS Appl. Mater. Interfaces, 2019, 11(45), 42671-42679.
[] [PMID: 31663328]
Zangade, S.; Chavan, S.; Vibhute, A.; Vibhute, Y. Synthesis and studies on antibacterial activity of some new chalcones and flavones containing naphthyl moiety. Sch. Res.Lib., 2011, 3, 20-27.
Pietta, P.G. Flavonoids as antioxidants. J. Nat. Prod., 2000, 63(7), 1035-1042.
[] [PMID: 10924197]
Cioffi, G.; Morales Escobar, L.; Braca, A.; De Tommasi, N. Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria. J. Nat. Prod., 2003, 66(8), 1061-1064.
[] [PMID: 12932124]
Isaac, R. SriBindu, M.C.; Reddy, P.S.; Joly, V.L.; Wu, R.J.; Murthy, C. Halogen substituted chalcone as potential antioxidants: An in vitro study. Adv. Sci. Eng. Med., 2012, 4, 499-505.
Witte, P.; Beuerle, F.; Hartnagel, U.; Lebovitz, R.; Savouchkina, A.; Sali, S.; Guldi, D.; Chronakis, N.; Hirsch, A. Water solubility, antioxidant activity and cytochrome C binding of four families of exohedral adducts of C60 and C70. Org. Biomol. Chem., 2007, 5(22), 3599-3613.
[] [PMID: 17971989]

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2020
Page: [145 - 156]
Pages: 12
DOI: 10.2174/2213335607666200129113827
Price: $25

Article Metrics

PDF: 16