Doláková Petra, Masojídková Milena, Holý Antonín
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Praha, Czech Republic.
Nucleosides Nucleotides Nucleic Acids. 2003 Dec;22(12):2145-60. doi: 10.1081/ncn-120026636.
Alkylation of 6-chloropurine and 2-amino-6-chloropurine with bromoacetaldehyde diethyl acetal afforded 6-chloro-9-(2,2-diethoxyethyl)purine (3a) and its 2-amino congener (3b). Treatment of compounds 3 with primary and secondary amines gave the N6-substituted adenines (5a-5c) and 2,6-diaminopurines (5d-5f). Hydrolysis of 3 resulted in hypoxanthine (6a) and guanine (6b) derivatives, while their reaction with thiourea led to 6-sulfanylpurine (7a) and 2-amino-6-sulfanylpurine (7b) compounds. Treatment with diluted acid followed by potassium cyanide treatment and acid hydrolysis afforded 6-substituted 3-(purin-9-yl)- and 3-(2-aminopurin-9-yl)-2-hydroxypropanoic acids (8-10). Reaction of compounds 3 with malonic acid in aqueous solution gave exclusively the product of isomerisation, 6-substituted 4-(purin-9-yl)-3-butenoic acids (15).
6-氯嘌呤和2-氨基-6-氯嘌呤与溴乙醛二乙缩醛进行烷基化反应，得到6-氯-9-(2,2-二乙氧基乙基)嘌呤(3a)及其2-氨基类似物(3b)。用伯胺和仲胺处理化合物3，得到N6-取代的腺嘌呤(5a - 5c)和2,6-二氨基嘌呤(5d - 5f)。3的水解反应生成次黄嘌呤(6a)和鸟嘌呤(6b)衍生物，而它们与硫脲反应则生成6-硫代嘌呤(7a)和2-氨基-6-硫代嘌呤(7b)化合物。先用稀酸处理，再用氰化钾处理，然后进行酸水解，得到6-取代的3-(嘌呤-9-基)-和3-(2-氨基嘌呤-9-基)-2-羟基丙酸(8 - 10)。化合物3与丙二酸在水溶液中反应，仅得到异构化产物，即6-取代的4-(嘌呤-9-基)-3-丁烯酸(15)。
