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Chalcone: a Versatile Molecule Chetana B ISSN:0975-1459 Chetana B Patil et al /J. Pharm. Sci. & Res. Vol.1(3), 2009, 11-22. Chalcone: A Versatile Molecule Chetana B. Patil*, S. K. Mahajan, Suvarna A. Katti Department of Pharmaceutical Chemistry, M. G. V’s Pharmacy College, Panchavati, Nashik-422003, Maharashtra, India. ________________________________________________________________________ ABSTRACT: Chalcones are 1,3-diphenyl-2-propene-1-one, in which two aromatic rings are linked by a three carbon α,β-unsaturated carbonyl system.These are abundant in edible plants and are considered to be precursors of flavonoids and isoflavonoids. The aim of this review to give summary of methods for synthesis of chalcones, its chemical modifications to flavonoids, flavanone, pyrazoles, oxazoles, pyrimidines. This article also highlights antioxidant potential of chalcone, mechanism of antioxidant activity of chalcones and structure activity relationship of chalcone derivatives for antioxidant ability and different methods to evaluate antioxidant activity of chalcone, anti- inflammatory, cytotoxic and antihyperglycemic activity of chalcones is also discussed in this review article. KEYWORDS: Antioxidant, chalcone, Claisen-schimdt reaction, MOM (methoxymethyl)-protected benzaldehyde ________________________________________________________________________ INTRODUCTION [1] Chalcones are synthesized by Chalcones are 1,3-diphenyl-2-propene- claisen-schmidt condensation of 1-one, in which two aromatic rings aldehyde and ketone by base are linked by a three carbon α, β- catalyzed or acid catalyzed followed unsaturated carbonyl system as, by dehydration to yield chalcones. O 6 2' 1 3 1' 5 3' A. Base catalyzed reaction [2][3][4] 1 2 A B The main method for the 4 2 6' 4' synthesis of chalcones is the classical 3 5' Claisen-Schmidt condensation in the Chalcone presence of aqueous alkaline bases. These are abundant in edible plants and are considered to be precursors Procedure [2] of flavonoids and isoflavonoids. Place a solution of 22g of sodium Chalcones possess conjugated hydroxide in 200ml of water and double bonds and a completely 100g (122.5ml) of rectified spirit in a delocalized Π-electron system on both 500ml bolt-head flask provided with benzene rings. Molecules possessing a mechanical Stirrer. Immerse the such system have flask in a bath of crushed ice, pour relatively low redox potentials and in 52g (0.43mol) of freshly distilled have a greater probability of acetophenone, start the stirrer and undergoing electron transfer reactions. then add 46g (44ml, 0.43mol) of 1. Methods for synthesis of chalcones: pure benzaldehyde. _________________________________ *For Correspondence Email: [email protected] 11 Chetana B Patil et al /J. Pharm. Sci. & Res. Vol.1(3), 2009, 11-22. Mechanism[2] H Ar H H2C Ar' Ar Ar' + NaOH O O O O Ketone Aldehyde + H H H Ar Ar' Ar Ar' -H2O OH O O Chalcone Keep the temperature of the mixture to litmus and then with 20ml of ice- at about 250C (the limits are 15- cold rectified spirit. The crude 300C) and stir vigorously until the chalcone after drying in the air 0 mixture is so thick that stirring is no weighs 88g and melts at 50-54 C. longer effective (2-3 hr). Remove the Recrystallized from rectified spirit 0 stirrer and leave the reaction mixture warmed to 50 C (about 5ml per g). in an ice chest or refrigerator The yield of pure overnight. Filter the product with benzylideneacetophenone (a pale 0 suction on a buchner funnel or a yellow solid) mp 56-57 C, is 77g (85%).This substance should be sintered glass funnel, wash with cold water until the washings are neutral handled with great care since it acts as a skin irritant. 12 Chetana B Patil et al /J. Pharm. Sci. & Res. Vol.1(3), 2009, 11-22. B. Acid catalyzed reaction: Mechanism[5] O OH OH CH 3 + H CH3 CH3 Acetophenone OH CH 2 + H O OH OH H + H H H Benzaldehyde H OH OH O H OH CH2 + H O H + H OH O H O H H H H OH OH2 H H - H3O O Chalcone 13 Chetana B Patil et al /J. Pharm. Sci. & Res. Vol.1(3), 2009, 11-22. Procedure [6] It is necessary to use protective group for the preparation of the To a stirred mixture of acetophenone hydroxy chalcones under basic (0.01mol) and benzaldehyde conditions. By using SOCl2 as a (0.01mol) in absolute ethanol (5ml), convenient alternative to the gaseous add thionyl chloride (0.05ml) HCl in the aldol condensation. dropwise and continue stirring for two hour at room temperature. Allow C. Methods for sy nthesis o f to stand reaction mixture for 12hr. chalcones having hydroxy Precipitate the reaction mixture by substituted aldehyde precursors[7] addition of water. Filter the product, The chalcone derivatives are prepare wash with cold ethanol. The yield of through base-catalyzed claisen-schimdt pure benzylideneacetophenone (a pale condensation of MOM-protected yellow solid) mp 56-570C, is 77.0g benzaldehydes with para- substituted (85%). acetophenones followed by acid catalyzed hydrolysis. In the reactions, the MOM- protected benzaldehydes In the presence of SOCl2/EtOH as a are used instead of non-protected catalyst various substituted chalcones dihydroxylated ones, because the are synthesized by aldol condensation. procedure with the free The HCl is generate in situ by the dihydroxylated benzaldehydes required reaction of SOCl2 with absolute long reaction time (more than one ethanol. day) and relatively high temperature (above 600C) which resulted in poor The aldol reaction is perform also yields with unknown degraded under acidic medium, using HCl, products. BF3, B2O3, p-toluene sulfonic acid, etc. The most common method The MOM group is proven to be the applies ethanol saturated with HCl. best choice. The MOM-protected The yields are low and vary between benzaldehydes which are readily 10% - 40%. According to the prepared by treating the corresponding literature data the presence of benzaldehydes with MOMCl in basic hydroxyl substituents in the aromatic condition (K2CO3/acetone), are aldehyde hinders the basic catalyze successfully converted to the chalcone aldol reaction. The reason behind that derivatives with diverse substitution is the fact that the basic catalysts patterns of two hydroxyl groups on decrease the activity of the aldehyde benzaldehyde origin ring B. Now the component because of delocalization hydroxyl protected chalcones are of the anion, which is illustrated deprotect in situ by acid hydrolysis below, to provide the desired final chalcone derivatives in good yields (>70%) with some exception. O B O O HO O O H BH H H Anion delocalization of the aldehydic component 14 Chetana B Patil et al /J. Pharm. Sci. & Res. Vol.1(3), 2009, 11-22. The relatively low yields for some 5 with 1N aqueous NaOH solution. products containing para- hydroxyl Extract the aqueous solution with acetophenone are consider probably EtoAc (20 ml x 3). Wash the organic due to the phenoxide ion formation layer with water (20 ml x 2) and brine from the acetophenone in the presence (20ml), dry over anhydrous MgSO4 of strong and excess amount of base. and evaporate to give a crude solid. The double bond geometry of all Purify resulting product by column chalcones is determine as E form the chromatography, elute with hexane- characteristic coupling constants ethyl acetate co-solvent to afford a between α and β protons. solid. I. Hydroxy benzaldehydes protect ed D. Microwave assisted synthesis[8] by MOM[7] The Claisen–Schmidt condensation Cool the solution of hydroxy stays the most common method in benzaldehyde (21.17 mmol) and homogeneous phase or in interfacial K2CO3 (217.20 mmol) in acetone solid-liquid conditions using barium (100ml) to 00C under Argon hydroxide catalyst (C-200). atmosphere and add Unfortunately 2’-hydroxychalcones methoxymethylchloride (MOM-Cl, always cyclized to flavanones. One 93.65 mmol) dropwise. Stir the synthetic pathway to avoid this resulting mixture at room temperature undesirable reaction is using for 6-10 hr. Dilute the reaction protective group or the Friedel–Crafts mixture with water (100ml) and reaction of phenols with acyl halides. extract with ethyl acetate (50ml x 3). This method request long reaction Wash organic layer with water and time and anhydrous conditions which brine, dry over anhydrous MgSO4 limits the scope of its application. and evaporate to dryness to yield Convenient reaction procedure for the crude MOM- protected benzaldehyde. synthesis of 2’-hydroxychalcones with Purify by silica gel column very good yields without formation of chromatography to give analytically by-products. By applying successful pure compounds (90-99%). microwave irradiation for the preparation of target molecules . The II. General syntheti c procedure for reaction took place in well closed the preparation o f pressure tube for 2 min with high dihydroxychalcones[7] yields. It is noteworthy to mention that To a solution of MOM-protected to carry out the reaction in an open benzaldehydes (0.9 mmol) and vessel failed. A mixture of two acetophenone (10mmol) in ethanol products (3 and 4) and starting (10ml), add 5% aqueous NaOH compounds was obtained in this case. (1.1mmol, 0.5ml). Stir the reaction Obviously, the well closed tube mixture at room temperature for 1-2 affords to reach temperatures much hr. Moniter the reaction, add 10% higher than boiling point of ethanol. HCl (1ml) and continue stirring for The measured temperature in the 30 min at 600C to deprotect the reaction tube immediately after the MOM groups. Dilute the mixture irradiation was 1320C. with water (20 ml) and adjust pH to 15 Chetana B Patil et al /J. Pharm. Sci. & Res. Vol.1(3), 2009, 11-22. R1 R2 CHO O O O R3 2 R R1 CH3 1 R R2 KOH/EtOH uW or 2 O OH 1320C OH 1 4 R 3 R3 3 2. Chemical modifications of dry with MgSO4 anhydrous. chalcones: Evaporate the solvent in vaccuo.
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