Indian Journal of Chemistry Vol. 48B, November 2009, pp. 1548-1557 Synthesis and biological activities of new 7-O-β-D-glucopyranosyloxy-3-(3-oxo-3- arylprop-1-enyl)-chromones K M Hatzade 1,2 , V S Taile 1 , P K Gaidhane 1 , V D Umare 1 , A G M Haldar 1 & V N Ingle* 1 1 Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur 440 033, India 2 Department of Applied Chemistry, SVSS College of Engineering & Research, Wanadongri, Hingna Road, Nagpur 441 110, India E-mail: g_kishor2000@yahoo.co.in Received 8 April 2008; accepted (revised) 16 April 2009 A convenient route to synthesize some new medicinally important 7-hydroxy-3-(3-oxo-3-arylprop-1-enyl)-chromones 2 is described by the interaction of 7-hydroxy-3-formyl chromone 1 with various substituted acetophenones which on condensation with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide affords 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy- 3-(3-oxo-3-arylprop-1-enyl)-4H-chromen-4-ones 3. Later on deacetylation with anhydrous zinc acetate in methanol gives 7-O-β-D-glucopyranosyloxy-3-(3-oxo-3-arylprop-1-enyl)-4H-chromen-4-ones 4. These compounds are evaluated for their in vitro antimicrobial and antioxidant activity. The structures of these newly synthesized compounds are established by IR, NMR, mass spectra, elemental analysis and chemical analysis. Keywords: Chromones, α, β-unsaturated carbonyl compounds, glucosylation, O-β-D-glucosides, biological activity In the last few years, glycobiology 1 has gained much attention because the oligosaccharide part of glycol- lipids, glycoproteins and other glycoconjugates are responsible for their function in various biological processes 2-10 . Although a large number of synthetic methods for glycoside formation have been developed 11-14 , but not all problems are well solved. The stereo- and regioselectivity increases by intramolecular O-glycoside bond formation 15 . In continuation of this work 16 , we report in this paper an efficient synthesis of α, β-unsaturated carbonyl compounds (chalcone) derived from 7-hydroxy-3- formyl-4H-chromen-4-one and substituted aceto- phenones and their O-glucosylation reaction in the absence of heavy metal salts but in the presence of DTMAB as a phase transfer catalyst leading to O-glucosides. Literature survey reveals the importance of chalcones as they possess antiinflammatory 17 , antibacterial 18 , antiviral 19 , insecticidal 20 , antimicro- bial 21 , gastric protectant 22 and antipicorhenovirus activities 23 . Similarly, several therapeutically interest- ing biological activities of chromones have been reported including anticancer 24-29 , anti-HIV 30-32 and antioxidant properties 33-35 . The remarkable biological properties of these categories of heterocycles oriented our attention to the synthesis of series of new heterocyclic derivatives combining chromonylidene acetophenone and carbohydrate moiety in one molecular frame as new possible biological active compounds. Herein, the synthesis of chalcones of hydroxy chromone and their O-glucosides starting from 7-hydroxy-3-formyl-4H-chromen-4-one is reported, together with the results on their biological activities. Results and Discussion During the course of the present investigation, the starting compound 7-hydroxy-3-formyl-4H-chromen- 4-one 1 required was synthesized by Vilsmeier-Haack reaction from resacetophenone 36 . The condensation 37 of 1 with substituted acetophenones in the presence of freshly distilled piperidine in dry absolute alcohol for about 2-3 hr has resulted in the formation of 7- hydroxy-3-(3-oxo-3-arylprop-1-enyl)-4H-chromen-4- ones 2. The IR spectrum of 2a showed a broad peak at 3348 cm -1 due to the OH stretch. The peaks at 3077, 2361 cm -1 were appeared due to Ar–CH stretch. A strong absorption at 1695 cm -1 was attributed due to α, β-unsaturated carbonyl C=O stretch. The peak at 1656 cm -1 was assigned to C=O stretching in γ- pyrone. The peaks at 1458 and 1090 cm -1 were due to