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Study on Synthesis and Anti-tumor Activity of Hydroxyflavone Derivatives

Author: HongXiuYun
Tutor: HuChun
School: Shenyang Pharmaceutical University
Course: Medicinal Chemistry
Keywords: Medicinal Chemistry Hydroxyflavone Derivatives Synthesis Anti-tumor activity
CLC: R914
Type: Master's thesis
Year: 2007
Downloads: 75
Quote: 0
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Abstract


Flavonoids are phytochemicals with the diverse beneficial effects, including anti-tumor, anti-inflammatory and anti-artherosclerosis activities, etc, which are ubiquitous in plants. In order to study the anti-tumor activity and structure-activity relationship, a series of hydroxyflavone derivatives and furan[2,3-h]flavone derivatives were designed and synthesized in this thesis.Nine hydroxyflavone compounds were synthsized with the flavone scaffold-constrcution by Baker-Venkataraman reaction. Fourteen hydroxyflavone derivatives and 4 furan[2,3-h]flavone derivatives were designed and synthesized on the base of hydroxyflavone derivatives as starting materials, which were characterized by IR, ~1H-NMR and ESI/MS, eighteen of which were not reported in literature based on the search by SciFinder and other database.3,8-Dichloro-7-hydroxyflavone is prepared by chlorination of 7-hydroxyflavone when methylene chloride as solvent in this thesis, whereas 3,6,8-trichloro-7-hydroxyflavone is prepared at same condition when carbon tetrachloride as solvent in literature.4’-Methoxy-7-hydroxyflavone is sulfonylated unexpectedly by concentrated sulfuric acid at 3’-position not 6- or 8-position.The anti-tumor activity of 4 target hydroxyflavone dervatives, i.e. 7-hydroxyflavone (HXY-01), 6-hydroxyflavone(HXY-07), 2’-methoxy-6-hydroxyflavone(HXY-08), 2’-chloro-6-hydroxy flavone (HXY-09) was tested in human leukemic HL-60 cells. All tested compounds exhibit anti-tumor activity, the median inhibitory dose of 2’-methoxy-6-hydroxyflavone is 7.68 micromole per liter.

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CLC: > Medicine, health > Pharmacy > Drug basic science > Medicinal Chemistry
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