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水楊酸2,2,2-三氯乙酯之合成及其生物活性

Synthesis and Biological Activities of 2,2,2-Trichloroethyl Salicylate

摘要


本研究係探討水楊酸2,2,2-三氯乙酯之合成,溶解度,水解速率及其生物活性。本製品由水楊酸及三氯乙醇在Dean-Stark反應器內,經酸催化脫水而得,熔點59℃。產品之特性由紫外光,紅外光吸收光譜,磁譜,質譜及元素分析確訂。本品對水之溶解度為0.8 mg/100 ml。動物實驗結果顯示本品之鎮痛及抗炎效果均較阿斯匹林或水楊酸為佳。本化合物於體外37℃時,對各種PH值之緩衝溶液皆難水解;但若加入PH=8之胰凝乳蛋白酶緩衝溶液,則分解成水楊酸。本前驅藥物可經酶水解而恢復原態,且具有與阿斯匹林類似之生物活性。

關鍵字

前驅藥物 鎮痛藥 抗炎藥

並列摘要


The synthesis, characterization, hydrolysis rate, and biological activities of 2,2,2-trichloroethyl salicylate were described. Catalytical esterification of salicylic acid with trichloroethanol in a Dean-Stark apparatus gave the title compound, mp. 59°C The compound was further characterized by UV, IR, NMR, and elemental analysis. In vivo, the compound showed significant analgetic and anti-inflammatory activities. In vitro, the compound is stable at various pH at 37°C. When α-chymotrypsin was added at pH 8, the compound was cleaved to be salicylic acid which was confirmed by TLC analysis.

並列關鍵字

Prodrugs Analgetics Antiinflammatory agents

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