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Synthesis and Anti-Inflammatory Activity of Novel Methyl Salicylate Derivatives

Author: YinYong
Tutor: YangHua
School: Guangxi University
Course: Applied Chemistry
Keywords: methyl salicylate derivatives piperazine anti-inflammatoryactivity synthesis
CLC: R965
Type: Master's thesis
Year: 2012
Downloads: 41
Quote: 0
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Salicylic acid drugs is a kind of chemicals with a wide range of biological activities,such as sterilization,anti-inflammatory,analgesic,antipyretic and so on. It belongs to a class of non-steroidal anti-inflammatory drugs(NSAIDs) and used clinically for antipyretic, analgesic and anti-inflammatory. In addition it has certain inhibition for tumors including pancreatic cancer, lung cancer, ovarian cancer and prostate cancer which have low-risk treatment.Piperazine as a kind of heterocyclic is commonly used in medicinal chemistry research, It can effectively adjust the drugs’ physicochemical properties,improve the pharmacokinetic properties and the biological activity by introducting it. Most of the compounds containing the piperazine have efficient pharmacological activity, and some have developed into clinical drugs.Based on the anti-inflammatory activity of salicylic acid and the piperazine can effectively improve the biological activity, sixteen novel structure of methyl salicylate derivatives with piperazine were designed and synthesized,and all the target compounds were characterized by IR,MS and1H-NMR.Two acute inflammation models, auricle swelling induced by xylol and paw edema swelling induced by carrageenan in mice were used to test the anti-inflammatory activity of the compounds. The results showed that all the compounds have significant inhibition of xylene-induced ear swelling and carrageenin-induced paw edema in mice (P<0.05or P<0.01).In the model of xylene induced the mice auricle swelling,compounds M2> M3、M4、M14、 M15and M16have anti-inflammatory activity superior to aspirin and indomethacin(P<0.05or P<0.01), the other compounds are comparable in anti-inflammatory activity to aspirin and indomethacin.In the model of carrageenan induced paw edema swelling, compounds M2、M14、M15and M16have anti-inflammatory activity superior to aspirin and indomethacin(P<0.05or P<0.01),the other compounds are comparable in anti-inflammatory activity to aspirin and indomethacin.Compounds M2、M14、M15and M16were used to test the dose-effect relationships. The results showed that compounds M2、M14、M15and M16have anti-inflammatory activity superior to aspirin and inferior to indomethacin.

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