| 摘要: | 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. |
