2-取代芐氧基苯甲酸衍生物之合成與生理活性; Synthesis and Biological Activities of 2-Substituted Benzyloxy Benzoic Acid Derivatives

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Title:	2-取代芐氧基苯甲酸衍生物之合成與生理活性;Synthesis and Biological Activities of 2-Substituted Benzyloxy Benzoic Acid Derivatives
Authors:	許書維;Hsu Shu-Wei
Contributors:	中國醫藥學院藥物化學研究所
Keywords:	芐氧基苯甲酸;抗下痢
Date:	1992
Issue Date:	2009-12-23
Abstract:	為了得到具有強力的抗過敏、抗發炎和抗下痢活性的化合物，著者以2-benzyloxybenzaldehyde為先導化合物，著手進行一系列2-substituted benzyloxy benzoic acid及其衍生物之合成。2-substituted benzyloxy benzonitriles 17-25, 2-substituted benzyloxy 2-methylbenzenes 26-29, 2-substituted benzyloxy phenyl methanols 30-33, 2-substituted benzyloxy benzoates 34-41, 2-substituted benzyloxy benzamides 42-44和2-substituted benzylamino benzoates 45-55是由substituted benzyl chloride在無水碳酸鉀及無水碘化鉀催化下，分別和2-氰基酚，鄰甲酚，柳酸，水楊酸甲酯，水楊醯胺，鄰氨基苯甲酸乙酯及2-氨基-4, 5-二甲氧基苯甲酸甲酯進行benzylation而得，另外，2-substituted benzyloxy benzoic acids 56-64及2-substituted benzylamino benzoic acids 65-75則是應用氫氧化鈉與相關之化合物進一步進行水解反應而得。將所合成之標的化合物進行生物活性之評估，發現2-substituted benzyloxy benzoic acid及其相關化合物對於抗發炎、抗過敏較不具活性。然而，2-[(4-methoxybenzyl)oxy] benzoic acid (64)和2-[(4-chlorobenzyl)amino] benzoic acid (68)對抗下痢則具有顯著的活性表現，值得進一步探討。; In order to obtain novel compounds with potent anti-inflammatory, anti-allergic and anti-diarrhea activities, 2-benzyloxybenzaldehyde was used as the lead compound, and 2-substituted benzyloxy benzoic acid derivatives were synthesized. 2-substituted benzyloxy benzonitriles 17-25, 2-substituted benzyloxy 2-methylbenzenes 26-29, 2-substituted benzyloxy phenyl methanols 30-33, 2-substituted benzyloxy benzoates 34-41, 2-substituted benzyloxy benzamides 42-44 and 2-substituted benzylamino benzoates 45-55 were synthesized by the benzylation with potassium carbonate and potassium iodide through the substituted benzyl chloride react with 2-cyanophenol, o-cresol, saligenin, methyl salicylate, salicylamide, ethyl anthranilate and methyl 2-amino-4,5- dimethoxybenzoate respectively. Then, the related compounds were hydrolyzed by sodium hydroxide to give 2-substituted benzyloxy benzoic acids 56-64 and 2-substituted benzylamino benzoic acids 65-75. After screening for their biological activities, most of them have no anti-inflammatory and anti-allergic activities. However, 2-[(4-methoxybenzyl) oxy] benzoic acid (64) and 2-[(4-chlorobenzyl) amino] benzoic acid (68) showed significant anti-diarrhea activities and worthy for further investigation.
Appears in Collections:	[Graduate Institute of Pharmaceutical Chemistry] Theses & dissertations

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Abstract.pdf	21Kb	Adobe PDF	333	View/Open
中文摘要.pdf	20Kb	Adobe PDF	512	View/Open
前段圖譜到60.pdf	6642Kb	Adobe PDF	424	View/Open
參考文獻.pdf	38Kb	Adobe PDF	412	View/Open
封面.pdf	20Kb	Adobe PDF	458	View/Open
後段圖譜.pdf	2753Kb	Adobe PDF	401	View/Open
書背.pdf	19Kb	Adobe PDF	555	View/Open
目錄.pdf	22Kb	Adobe PDF	497	View/Open
第一章緒論之修改版.pdf	175Kb	Adobe PDF	1321	View/Open
第三章結論.pdf	23Kb	Adobe PDF	615	View/Open
第二章結果與討論修改版.pdf	898Kb	Adobe PDF	647	View/Open
第二章結果與討論之後段.pdf	686Kb	Adobe PDF	565	View/Open
第四章實驗部分.pdf	154Kb	Adobe PDF	1234	View/Open
謝辭.pdf	20Kb	Adobe PDF	747	View/Open

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