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Synthesis of 7-hydroxy Isoflavone Ferulate Derivatives and Evaluation of Their Relative Activities

Author: ZhouBeiDou
Tutor: ZhengJinHong
School: Shantou University
Course: Medicinal Chemistry
Keywords: synthesis isoflavone ferulic acid
CLC: R285
Type: Master's thesis
Year: 2009
Downloads: 52
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Abstract


Ferulic acid is a phenolic antioxidant.It mainly exits in angelica、rhizoma chuanxiong and radix cyathulae. It has the pharmacological activities of antioxidation,anti-thrombosis, scavenging free radicals, inhibiting platelet congregation and so on. Isoflavone is floristic female hormone.It has extensive physiological activities in body.Which has activities of anti-tumor,enhancing anti-oxidated enzyme,preventing vascular disease,slowering tendency of senes- -cence,curing neuropathic disease and so on.Now we design that carboxyl of ferulic acid and hydroxyl of isoflavone are esterified condensably .We expect new compounds can work synergistic pharmacological activities.At first we esterify the hydroxyl of ferulic acid from thinking of synthetic technics. So target compounds will become prodrug.They will work after enzyme action or enzyme hydrolysis in body. Their liposolubility increases and their bioavailability may be enhanced after the modification.We have found a feasible synthetic route after experi- -ment.At last we measure their influence for central antioxidation in the brain tissues of scopolamine-induced gawkish mice.1、Synthesis of 7-hydroxy isoflavone ferulate derivativesObjective: To synthesize 7-hydroxy isoflavone ferulate derivativesMethods: Resorcinol and para-substituted phenylacetic acid took place Friedel-Craft reaction.Under the catalysis of PCl5 ,their products were cyclized by dimethylformamide (DMF).At last 7-hydroxy isoflavone and its derivatives were synthesized.Ferulic acid and its derivatives were synthesized from substituted para-hydroxy benzaldehyde through Knoevenagel condensable reaction.At first the phenolic hydroxyl of ferulic acid or its derivatives was esterified by ethyl chloroformate , then its carboxyl was made to acyl chloride.Finally it took place esterifiable reaction between acyl chloride and isoflavone.Results: 8 target compounds were synthesized. Their structures were confirmed by 1HNMR、MS and IR. Conclusion: A feasible synthetic route was found after experiment.2. Target compounds were tested in the scopolamine-induced gawkish mice, for evaluating their influence for central antioxidation.Objective: To evaluate their influence for central antioxidation in the mice.Methods: Maybe Compound T4 has better activities,so it was chose to make pharm- -acological experiment. The activities of glutathione peroxidase (GSH-PX) and superoxide dismutase (SOD)、the level of malondialdehyde (MDA) were measured in brain tissues of scopolamine-induced gawkish mice.Results: Compound T4 could enhance central antioxidation as compared with the model group.Conclusion: This kind of compounds can prevent cardiovascular diseases.Their potential can be tested in curing Alzheimer’s disease. Their pharmacological activities deserve to be studied further.

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