Efficient microwave synthesis of coumarin derivatives with evaluation of their antioxidant and anti-inflammatory properties
Abstract
Microwave radiation, an electromagnetic radiation, is used as a source of heating in organic synthesis. Coumarin, a benzopyrone derivative, shows various pharmacological activities such as anticoagulant, antimicrobial, analgesic, anti-inflammatory. The prime objective was to compare the synthesis of some coumarin derivatives by microwave assisted methods. Two different coumarin derivatives were synthesized and evaluated for their anti-inflammatory activity and anti-oxidant activity. 3-Acetylcoumarin (3-acetyl-2H-Chromen-2- one) was synthesized by reaction with salicylaldehyde and ethyl acetoacetate in presence of piperidine and the 3-acetyl-6-bromocoumarin (3-acetyl-6-bromo-2H-chromen-2-one) was synthesized by using 5-bromo-salicyladehyde. The synthesized compounds were characterized by MP, TLC, IR and NMR. The antioxidant activity of the compounds was done by reducing power by ferric chloride, nitric oxide and hydrogen peroxide scavenging method. The anti-inflammatory activity of the compounds was done by protein denaturation using BSA method. Out of the two compounds synthesized, bromine-substituted acetyl coumarin showed more anti-oxidant and anti-inflammatory activity when compared to standard.
Keywords:
Microwave radiation, Coumarin, Anti-oxidant, Anti-inflammatory
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References
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2. Sabry NM, Mohamed HN, Shawky E, Khattb AFH. Synthesis of 4H- chromenes, coumarin, 12-H chromeno (2,3, d) pyrimidine derivatives and some of their anti-microbial and cytotoxic activity. J Euro Med Chem. 2011; 46:765-772
3. Pelle L. Microwave assisted organic synthesis-a review tetrahedron. Aust J Chem 2001:9225-9283
4. Gopalakrishnan M et al. Microwave assisted multicomponent reaction for the synthesis of, 4-dihydropyrimidin-2(1H)-ones and their corresponding 2 (1 H)-thiones using lanthanum oxidase a catalyst under solvent-free conditions. Arab J Chem June 2011; 1-4
5.Gnanamanishanthi, Paramashivan T P. Urmila R. Sehgal P. K. Synthesis and antioxidant activity of coumarins Indi J Chem 2009 48 131-132
6. Belsare D. Paul S, Kazi A, Kankate L Vanjari D. Evaluation of antioxidant activity of chalcones and flavonoids. Inter J Chem Tech Res 2010; 2:1080-1080
7. Chi-rein, Wumei-wueh-hueng, Yung-talin. Anti-oxidant properties of cortex fraxini and its simple coumarins. J Food Chem 2007, 104:2094-1749
8. Tyagi S N, Rakshit V, Singh A, Raghavendra D, Saxena A. Patel B D Invitro antioxidant activity of methanolic and aqueous extract of Flacourtiaindica. JAmer-Eurasian sci Res 2010,5(3) 201-206
9. Indulatha VN, Gopal N, Jayakar B Anti-inflammatory activity of newly synthesized n[4’-oxo-2’-sustituted aryl /hetaryl)-thiazolidin-3’-yl]-3’-carboxamide -2H-chromene-2-one-derivatives Inter J Chem Toch Res. 2011, 3:1930-1937
10 John V. Regina B Inflammation and the mechanism of action of anti- inflammatory drags. The J FASEB Rev 1987; 18996
11 Sharma YR Elementary organic spectroscopy principles and chemical applications. 5th ed Delhi: S. Chand publications; 2013; p 75,
12 Sharma YR Elementary organic spectroscopy principles and chemical applications. 5th ed. Delhi: S. Chand publications, 2013; p.191
13. Hocine A, Faouzi E, Guenadil E, Kapanda CN, Didier E M. Synthesis and pharmacological evaluation of antioxidant chalcone derivatives of 2(3H)-benzoxazolones. J Med Chem Res 2009, 18:467-476
14. Chetan BS, Nimesh M S. Manish P. Patel R G Microwave-assisted synthesis of novel 4H-chromene derivatives bearing phenoxy pyrazole and their antimicrobial activity assessment. Serb J Chem Soc. 2012;77(9):1165-1174
15. Rafik R, Koussinia B, Al-Shihria AS Microwave-Assisted Synthesis of 3-Nitro-2H-Chromenes Under Solvent-less Phase-transfer catalytic conditions. Jord J Chem 2008;3103-3107.
16. Arora S, Venugopal KN. Jayashree BS Microwave assisted synthesis of substituted coumarinyl chalcones as reaction intermediate for biologically important coumarinyl and heterocycles. Asian of Chem. Vol20:2008: 1-7/
17 Venkateswara R K, Murthy V.S.A convenient one step synthesis of 3-acetyl-4- hydroxy coumarin Proc. Indian Acad Sci. Vol 81, Issue 3: pp-118-123.
18 El-Agrody A, El-Latifil M, El-Fakery H N, Beadir A A. Hetero aromatization with 4-hydroxy coumarin part II: Synthesis of some new pyrano [2,3- d] pyrimidine, [1,2,4] triazolo[1,5-c] pyrimidine and pyrimido[1,6-b] [1,2,4] triazine derivatives. Molecules 2001; 6:519-527
19 Rajasekaran S, Gopalkrishna Rao, Sanjay P N. Gurpreet Singh Sodhi Synthesis, Antibacterial and invitro Antioxidant Activity of 2,3-Substituted Quinazolin-4(3H)-ones. J. Chem. Pharm. Res. 2010;2(1):482-488
20 Virendra Singh et al Invitro Antioxidant Activity and Phytochemical Analysis of Stem Bark of Blanites roxburghii Planch. Advances in Bio Res. 2009, 3(5- 6):242-246
21 Kadhum AAH, Ahmed AA, Amiery AYM and Mohamed AB. The antioxidant activity of new coumarin derivatives Int J Mol Sci 2011;12(9) 5747-5761
22 Patel K S, Patel J C, Dholariya H R, Kanuprasad D. Studies of newly synthesized octahedral copper complexes based on-bromo-coumarins along with their antioxidant, anti-tubercular and antimicrobial activity evaluation Open J Met Vol 96, 2012; 468-479
23. Singh O M, Devi N S, Sharma GS, Novel 3-alkanoyl/aroyl/hetero aroyl-2H- Chorome-2-thiones Synthesis and evaluation of their anti-oxidant activities. Eur Med Chem. 2010; 45:2250-2257
24 Kasumbwe K, Venugopala K N, Yadhav V. Mohanlall V B. Antioxidant and antimicrobial activities of substituted halogenated coumarins J Med Plant Res Vol 8(5),2014,274-281.
25 Ghate MR, Kusanur R A. Kulkarni MV Synthesis and In vivo analgesic and anti-inflammatory activity of some bi-heterocyclic coumarin derivatives Eur J Med Chem. vol 40; issue 9:2005; 882-887
26. Chaudhari A, Sharma P K, Verma P. Kumar N, Dathe R. Microwave assisted synthesis of novel pyrimidine derivatives and investigation of the anti-inflammatory and analgesic activity Med Chem Res.vol 19,2010, issue 2:9-21.
27 Leadbeater N E, Schmink JR. Use of Raman spectroscopy as a tool for insitu monitoring of microwave promoted reactions. Nat Proto 2008,3:1-7,
28 Nicolas E. Leadbeater & Jason. R. Schmink "Use of Raman Spectroscopy as a tool for in situ monitoring of microwave promoted reactions" Nature protocols (2007)
29 Nicolas E Leadbeater & Jason R. Schmink. "Use of Raman Spectroscopy as a tool for in situ monitoring of microwave promoted reactions" Nature protocols3,1-7 (2008)
Published
30/11/2023
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P A, A., T S, S., K, A., Krishna, A., Baby, S., & Daniel, D. P. (2023). Efficient microwave synthesis of coumarin derivatives with evaluation of their antioxidant and anti-inflammatory properties. Journal of Innovations in Applied Pharmaceutical Science (JIAPS), 8(3-S), 124-130. https://doi.org/10.37022/jiaps.v8i3-S.523
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