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Studies On The Synthesis And Antioxidant Activity Of Novel Curcumin Analogues

Posted on:2011-10-18Degree:MasterType:Thesis
Country:ChinaCandidate:S Z WangFull Text:PDF
GTID:2154330332465334Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Curcumin is a naturally yellow pigment. It is obtained from the rhizomes of curcuma longa. Curcumin is an important condiment that is used to add flavour and colour to food and also has an important medicinal value. It exhibits a veriety of pharmacological activities including antitumor, antiinflammation, antioxoidant, anti-HIV, and anti-Alzheimer's disease. Curcumin is very safe which hasn't shown any side effect to human. In this work, based on the knowledge of structure-activity relationship (SAR) and some new curcumin analogues were designed and synthesized, and their antioxoidant activities were determinated with DPPH method.Curcumin analogues A1,A2,A3 were synthesized by the condensation of complex formed by boron oxide and acethylacetone with indole-3-carboxaldehyde and 5-methoxyindole-3- arboxaldehyde respectively, with ethyl acetate as solvent and n-butylamine as catalyst. Curcumin derivative B1 was synthesized by several steps, which was formed introducing a hydrophilic group diethylene glycol monomethylether to the curcumin. Curcumin analogues C1,C2,C3,C4,C6,C7,C8,C9,C10,C11,C12,D1,D2 were synthesized by the condensation of aldehyde with cyclopentanone or cyclohexanone respectively with piperidine as catalyst in ethylene glycol. Curcumin analogues C5 were obtained through aldehydes and cyclopentanone in 30% sodium hydroxide solution by Claisen-Schimdt reaction. The solvents and catalysts were selected in Claisen-Schimdt reaction. The project of L9 (34 ) orthogonal test for A1 was designed. Two synthetic methords of C3 were compared. These products were confirmed by UV-Vis, IR, 1H NMR and MS spectra.The antioxidant abilities of curcumin analogues were investigated by DPPH radical scavenging assay in 5 concentrations respectively. The products had shown certain antioxidant activity. The antioxidant abilities were enhanced with the increase of concentration or time. The products of A2,C8,C9 showed better antioxidant activities.
Keywords/Search Tags:curcumin analogues, synthesis, DPPH, antioxidant activity
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