- Synthesis method of isolicoflavonol
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The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.
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Paragraph 0111; 0274-0280
(2020/12/29)
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- 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
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4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
- De Meyer,Haemers,Mishra,Pandey,Pieters,Vanden Berghe,Vlietinck
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p. 736 - 746
(2007/10/02)
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- ANTIMICROBIAL FLAVONOIDS FROM PSIADIA TRINERVIA AND THEIR METHYLATED AND ACETYLATED DERIVATIVES
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Key Word Index - Psiadia trinervia; Compositae; flavonoids; antifungal; antibacterial; Cladosporium cucumerinum; Bacillus cereus; bioautography.Abstract - From a dichloromethane extract and a hydrolysed methanolic extract from the leaves of Psiadia trinervia, 13 3-methylated flavonol have beeen isolated.Their structures were established by the usual spectoscopic methods (UV, EIMS, 1H and 13CNMR).Ayanin, casticin, chrysosplenol-D and 5,7,4'-trihydroxy-3,8-dimethoxyflavone were responsible for the antifungal activity found in the preliminary screening.Chrysosplenol-D, isokaemferide, 5,7,4'-trihydroxy-3,3'-dimethoxyflavone and 5,7,4'-trihydroxy-3,8-dimethoxyflavone displayed antibacterial activity.Twenty-nine derivatives were prepared by permethylation and selective methylation of the free hydroxyl group at C-5.The antimicrobial activities of the isolates and derivatives were determined by bioautographic assays using C. cucumerinum and B. cereus as test organisms.
- Wang, Ying,Hamburger, Matthias,Gueho, Joseph,Hostettmann, Kurt
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p. 2323 - 2328
(2007/10/02)
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