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Current Trends in Biotechnology and PharmacyVol. 5 (1) 1021-1028 January 2011. ISSN 0973-8916 (Print), 2230-7303 (Online)1027Table 1. Anti-Inflammatory activity of ChalconesCompound Ar % inhibition ± SEM atvarious time intervals0.5h 1.0h 2.0h 3.0h 4.0h 6.0hB 12'’-pyridinyl 6±1 7±1 37±1 45±1 76±1 78±1B 23'’-pyridinyl 6±1 7±1 36±1 45±1 75±1 77±1B 34'’-pyridinyl 6±1 7±1 35±1 46±1 74±1 78±1B 42'’-furyl 5±1 6±1 33±1 45±1 72±1 75±1B 52'’-pyrrolyl 13±1 15±1 52±1 64±1 93±1 97±1B 62'’-thienyl 7±1 9±1 39±1 50±1 79±1 80±1B 72'’-indolyl 14±1 17±1 54±1 65±1 95±1 98±1B 82'’-quinolinyl 7±1 8±1 38±1 48±1 77±1 79±1B 99'’-anthracenyl 10±1 12±1 45±1 56±1 85±1 90±1B 104'’-fluorophenyl 9±1 11±1 43±1 55±1 82±1 87±1B 114'’-chlorophenyl 8±1 11±1 42±1 53±1 81±1 85±1B 124'’-bromophenyl 8±1 10±1 40±1 52±1 80±1 82±1B 134'’-methylphenyl 12±1 13±1 49±1 58±1 90±1 94±1B 144'’-methoxyphenyl 11±1 13±1 47±1 57±1 88±1 91±1B 153'’,4'’,5'’-trimethoxyphenyl 13±1 14±1 51±1 61±1 92±1 95±1Aceclofenac (standard) 21±1 23±1 56±1 67±1 96±1 99±1Results and DiscussionThe anti-inflammatory activity of thesome newly synthesized chalcones (B 1-B 15) hasbeen evaluated by using carrageenan-induced ratpaw oedema method. The results of the evaluationhave been viewed by taking aceclofenac as thestandard drug.The results of anti-inflammatory activityrevealed that the compounds B 1to B 15exhibitedmoderate to considerable activity when comparedwith reference standard aceclofenac, but not atan identical dose level as the standard drug wastested at 2 mg/kg, whereas the chalcones weretested at a dose of 10 mg/kg.From the results it is evident that all thechalcones showed some degree of antiinflammatoryactivity. However, it is found thatthe chalcone having indole substituent (B 7)displayed significant anti-inflammatory activityfrom 3 rd hour onwards and reached the maximumat the 6 th hour and is comparable to that of thestandard aceclofenac, but not at an identical doselevel. This type of anti-inflammatory activity forthis chalcone is understandable since indolederivatives are known to possess significant antiinflammatoryactivity and a number of drugsbelonging to this class are also being used as aNSAIDs. But what is worth noticing is theretention of such activity even in the case ofchalcones bearing this moiety. This suggestschalcones can be prepared having othersubstituted indole moieties in order to enhancethe activity further. The next compound in orderof potency is the one having a pyrrole substituent(B 5). This was followed by compounds havingSynthesis and Anti-Inflammatory
Current Trends in Biotechnology and PharmacyVol. 5 (1) 1021-1028 January 2011. ISSN 0973-8916 (Print), 2230-7303 (Online)1028electron releasing groups as seen in the case ofcompound B 15, B 13and B 14. This clearly revealsthe importance of electron releasing groups onthe aromatic ring in enhancing the antiinflammatoryactivity and hence attempts can bemade to synthesize chalcones having a numberof such electron releasing substituents at differentpositions of the aromatic ring as part of preparingmore potent compounds.However, the contributing physicochemicalproperties for the anti-inflammatoryactivity of the chalcones need to be establishedby detailed QSAR studies, which may provideinsights into the structural requirements of thisclass of molecules. Further studies are requiredto establish the mechanism of anti-inflammatoryactivity of these compounds, even though literaturereports suggest the inhibition of COX-2 enzymein some cases.ConclusionsChalcones with heterocyclic nucleussuch as indole, pyrrole and also the substituentswith electron releasing groups such as methoxy,methyl showed better anti-inflammatory activity.Compounds having pharmacophores such asfluoro, chloro, bromo groups have exhibitedmoderate anti-inflammatory activity. These resultssuggest that’s the chalcone derivatives haveexcellent scope for further development ascommercial anti-inflammatory agents.References1. Bohm, B.A. (1998) In: Introduction toFlavanoids, Harwood Academic Publishers,Amsterdam.2. Kumar, S.K., Hager, E., Pettit, C.,Gurulingappa, H., Davidson, N.E. andKhan, S.R. (2003) Design, synthesis andevaluation of novel boronicchalcone derivativesas antitumor agents. J.Med.Chem., 46:2813.3. Mukarami, S., Muramatsu, M., Aihara, H.and Otomo, S. (1991) Inhibition of gastricH + , K + -ATPase by the antiulcer agentSofalcone. Biochem. Pharmacol., 42: 1447.4. Viana, G.S., Bandeira, M. A. and Matos, F.(2003) Analgesic and anti-inflammatory effectsof chalcones isolated fromMyracrodruonurundeuva.J.Phytomedicine., 10:189.5. Onyilagna, J.C., Malhotra, B., Elder, M. andTowers, G.H.N. (1997) Synthesis andantimicrobial activity of some chalconederivatives. Can.J.Plant Pathol., 19: 133.6. Liu, M., Wilairat, P. and Go, L.M (2001)Antimalarial alkoxylated and hydroxylatedchalcones: structure-activity relationshipanalysis. J.Med.Chem., 44: 4443.7. Chen, Z-H., Zheng, C-Ji., Sun, L-P. and Piao,H-R. (2010) Synthesis of new chalconederivatives containing a rhodanine-3-aceticacid moiety with potential antibacterialactivity. Eur. J. Med. Chem., 45: 5739.8. Prasad, Y.R., Kumar, P.R., Deepti, Ch.A.and Ramana, M.V. (2007) Synthesis andantimicrobial activity of some chalcones of3-acetylcoumarin and 2-hydroxy-1-acetonaphthone.Asian.J.Chem., 19: 4799.9. Prasad, Y.R., Kumar, P.R., Srivani, N. andRao, A.S. (2006) Synthesis and antimicrobialactivity of some new chalcone derivatives.Int.J.Chem.Sci., 44: 905.10. Turner, R.A. (1965) In: Screening Methodsin Pharmacology, Demic Press, NewYork,p. 152.11. Winter, C.A., Risley, E.A. and Nuss, G.W.(1962) Carrageenan induced edema in hindpaw of the rat as an assay for anti-inflammatorydrugs. Proc. Soc. Exp. Biol. Med.,111: 544.Srinadh et al
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