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Synthesis and structural modification of the stilbene compounds with biological activity

Author: GaoJunFeng
Tutor: FangZhiJie
School: Nanjing University of Technology and Engineering
Course: Biochemical Engineering
Keywords: stilbenes synthesis structure modification tumor cells leading compounds alkylation glycosylation
CLC: O621
Type: Master's thesis
Year: 2005
Downloads: 261
Quote: 0
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Abstract


In this thesis, the synthesis and its structure modification of bioactive stilbenes have been studied.55 stilbenes were synthesized, including 16 simple stilbenes and 20 modified products. Notably, 4 compounds, 1, 3, 4 and 6 have anticancer activity according to biological activity tests. As leading compounds these stilenes were modified by alkylation, glycosylation and association on the basis of the theory of structure modification and the theory of structure-activity relationships.Substituted benzaldehyde was modified by alkylation and the corresponding intermediate was synthesized. These intermediates reacted with substituted phenylacetonitrile to synthesize alkylation modified products. 10 products were synthesized which have 4 new compounds.Substituted benzaldehyde or substituted phenylacetonitrile was modified by glycosyl respectively. The corresponding glycopyranoside intermediates were synthesized, and they reacted with substituted phenylacetonitrile or substituted benzaldehyde to synthesize glycosylation modified products. 23 products were synthesized which have 14 new compounds.The p-aminobenzene sulfpnamide group was connected to stilbene skeleton of stilbenes, and many twin drugs were prepared.In addition, some aryl-substituted propenoic acids were prepared via Perkin reaction. The cyclization and decarboxylation reaction were studied.Finally, Most of the pure products above were analyzed by HPLC and their structures were confirmed by ~1NMR, IR and MS etc.. Biological activity tests showed that these modified products also have anticancer activity.

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