full issue - Association of Biotechnology and Pharmacy

Current Trends in Biotechnology and PharmacyVol. 5 (1) 1021-1028 January 2011. ISSN 0973-8916 (Print), 2230-7303 (Online)Synthesis and Anti-Inflammatory Activity of some NewChalcones from 3' - Methyl- 4' – Hydroxyacetophenone1021N. Srinath * , Y. Rajendra Prasasd 1 , K. Mukkanti 2 , C. Kistayya 1 and B. Bhaskar Rao 1Department of Pharmacy, Acharya Nagarjuna University, Guntur – 521250, A.P., India1University College of Pharmaceutical Sciences, Andhra University,Visakhapatnam-530003, A.P., India2Centre for Pharmaceutical Sciences, J N T University, Hyderabad – 500085*For Correspondence - srinath_n2k@rediffmail.comAbstractA series of some new chalcones weresynthesized by Claisen-Schmidt condensation of3'-methyl-4'-hydroxyacetophenone with varioussubstituted aromatic / heteroaromatic aldehydesin the presence of alkali. The resulting chalconeswere characterized by IR, 1 H NMR and Elementalanalysis. These chalcones were evaluatedfor their anti-inflammatory activity and some ofthem exhibited significant activity when comparedwith the standard.Key words: Chalcones, Synthesis, Anti-inflammatoryactivityIntroductionChalcone is a generic term given to compoundsbearing the 1, 3-diphenylprop-2-en-1-oneframe work, which can be functionalized in thepropane chain by the presence of olefinic, ketoand / or hydroxyl groups (Fig.1) (1). Chalconeshave been reported to exhibit a wide variety ofpharmacological activities including antioncogenic(2), antiulcerative (3), analgesic and anti-inflammatory(4), antiviral (5), antimalarial (6) and antibacterial(7) activities. The presence of a reactiveá, â – unsaturated keto function is partly responsiblefor their activities. Chalcones are readilysynthesized by the base catalyzed Claisen –Schmidt condensation of an aldehyde and an appropriateketone in a polar solvent like ethanoland yields may be variable (8,9) ranging from 5to 80%. In the present communication, we reportthe reaction of 3'-methyl-4'-hydroxyacetophenonewith different aromatic / heteroaromatic aldehydesto form chalcones (B 1–B 15). The structures ofall the synthesized compounds were assigned onthe basis of IR, 1 H NMR spectral data and Elementalanalysis. These compounds were alsoscreened for their anti-inflammatory activity.Fig.1ExperimentalMelting points were determined in opencapillary tubes and are uncorrected. The IR spectrawere recorded in KBr on Perkin Elmer – 337Infrared Spectrophotometer. The 1 H NMR wererecorded in CDCl 3on Bruker AMX 400MHzNMR Spectrophotometer using TMS as an internalstandard. The Elemental analysis was performedon Perkin Elmer model 2400 series IIapparatus. The purity of the compounds waschecked by TLC using Silica gel-G (Merck).Column chromatography was performed on Silicagel (Merck, 60-120 mesh).Synthesis and Anti-Inflammatory