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常用中药使君子的驱蛔虫有效成份为使君子氨酸(quisqualic acid),其结构证明为L-β-(3,5-二氧-1,2,4-(口恶)二唑烷基-2)-丙氨酸(Ⅰ)。Ⅰ的红外光谱(图1)证实为一氨基酸,v_(NH(NH_3~+)) 3000,2860,2740厘米~(-1);δ_(as(NH_3~+))1614厘米~(-1);δ_s(NH_3~+))1500厘米~(-1);v_(COO)-1630厘米~(-1)。1755和1785厘米~(-1)二吸收峰可能由于v_(C=O)和V_(C=O(N-O-C=O))所引起。核磁共振谱为:δ4.60(二重峰,2H,β-CH_2);84.76(三连峰,1H,αCH)。使君子氨酸(Ⅰ),C_5H_7N_3O_5,以盐酸水解生成二氧化碳,氯化铵和d1-α,β-二氮基-丙酸盐酸盐(Ⅱ),Ⅰ以Pd-C为催化剂在甲醛存在下进行氢化,产物经水解后通过阴离子交换树脂,再以过氯酸处理,即得d1-α-二甲氨基-β-氨基-丙酸过氯酸盐(Ⅳ)。Ⅰ与苯甲酰氯作用生成N~a-苯甲酰-使君子氨酸(Ⅷ),C_(12)H_(11)N_3O_6。 后者以重氮甲烷处理即得N~a-苯甲酰-N~4-甲基-使君子氨酸甲酯(Ⅸ),C_(14)H_(15)N_3O_6。Ⅸ在甲醇中以硼氢化钠还原生成N~a-苯甲酰-N~4-甲基-使君子氨酵(Ⅹ),C_(13)H_(15)N_3O_5,此化合物水解后可获苯甲酸和N~4-甲基-使君子氨醇氢溴酸盐(Ⅺ),C_6H_(11)N_3O_4·HBr,后者继续水解即生成2,3-二氨基-丙醇双氢溴酸盐(Ⅻ)。实验结果推定使君子氨酸的结构式为Ⅰ。作者合成
Common Chinese medicine to make the gentleman’s roundworm effective component is quisqualic acid (quisqualic acid), the structure proved to be L-β- (3,5-dioxo-1,2,4-oxalacetadiazolidinyl- 2) -alanine (I). The infrared spectrum of Ⅰ was confirmed to be an amino acid. The results showed that there was no significant difference between the two groups (p <0.05) ; δ_s (NH_3 ~ +)) 1500 cm -1; v_ (COO) -1630 cm -1. The 1755 and 1785 cm -1 two absorption peaks may be caused by v_ (C = O) and V_ (C = O (N-O-C = O)). Nuclear magnetic resonance spectrum:? 4.60 (doublet, 2H,? -CH?); 84.76 (triplet, 1H,? CH). (Ⅰ), C_5H_7N_3O_5, with hydrochloric acid hydrolysis to generate carbon dioxide, ammonium chloride and d1-α, β-diazepin-propionic acid hydrochloride (Ⅱ), Pd-C catalyst Ⅰ in the presence of formaldehyde Hydrogenation, the product after hydrolysis by anion exchange resin, and then treated with perchloric acid, that d1-α-dimethylamino-β-amino-propionic acid perchlorate (Ⅳ). Ⅰ and benzoyl chloride to produce N ~ a-benzoyl - soildonine (Ⅷ), C_ (12) H_ (11) N_3O_6. The latter is treated with diazomethane N ~ a-benzoyl-N ~ 4-methyl - somatoside methyl ester (IX), C_ (14) H_ (15) N_3O_6. IX reduction with sodium borohydride in methanol to produce N ~ a-benzoyl-N ~ 4-methyl - so that the fermentation of a compound of ammonia (Ⅹ), C_ (13) H_ (15) N_3O_5, this compound can be benzene Formic acid and N ~ 4-methyl-quercetin hydrobromide (Ⅺ), C_6H_ (11) N_3O_4 · HBr, which continue to hydrolyze 2,3-diamino-propanol dihydrobromide ( Ⅻ). The experimental results presumed that the structure of Quisqualine Ⅰ. Author synthesis