Ecofriendly Synthesis and Characterization of Glucoside Derivatives and Its Biological Evaluation
Keywords:
Guanidine, Pyrimidine, Glucoside, antimicrobial activityAbstract
Ethyl 2-imino-6-methyl-4-substituted phenyl-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate compounds [4a-g] were achieved via a one pot multicomponent reaction of ethyl acetoacetate, substituted aromatic aldehyde with guanidine. The reaction is efficiently endorsed to give the preferred products in high yields and in a moderately short time. The resulted pyrimidine derivatives [4a-g] were treated with 2, 3, 4, 6-tetra-O-acetyl-?-D-glucopyranosyl bromide, potassium hydroxide mixed into 1 gm of neutral alumina in solvent free microwave condition furnished a (2S, 3S, 4R, 5S)-2-(acetoxymethyl)-6-((5-(ethoxycarbonyl)-4-methyl-6-phenyl-1, 6-dihydropyrimidin-2-yl)amino) tetrahydro-2H-pyran-3,4,5-triyl triacetate [5a-g]. The resulted products be deacetylated using methanol and ammonia furnished a Ethyl 6- (substituted phenyl) -4- methyl -2- (((3S, 4R, 5R, 6S)-3, 4, 5-trihydroxy -6- (hydroxyl methyl) tetra hydro-2H-pyran-2-yl) amino)-1,6-dihydropyrimidine-5-carboxylate[6a-g]. The molecular structures of the novel synthesized compounds were revealed based on their spectral analysis and elemental analysis. The purity of all synthesized compounds was resoluted by TLC. In addition, preferred derivatives of the products were screened for antimicrobial activity and there in vitro antioxidant activity. The antioxidant activity of the resulted products was also examined and most of them exhibited potent activity.
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