Synthesis of base substituted 2-hydroxy-3-(purin-9-yl)-propanoic acids and 4-(purin-9-yl)-3-butenoic acids.
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).
Doláková
Petra
P
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Praha, Czech Republic.
Masojídková
Milena
M
Holý
Antonín
A
D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000737:chemistry; D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D002087:Butyrates / Q000737:chemistry; D006147:Guanine / Q000031:analogs & derivatives; D007042:Hypoxanthines / Q000737:chemistry; D019344:Lactic Acid / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D002087:Butyrates; D007042:Hypoxanthines; D011687:Purines; C063782:6-amino-2-chloropurine; D019344:Lactic Acid; D015075:2-Aminopurine; C007300:2,6-diaminopurine; D006147:Guanine; C479121:3-butenoic acid; C045526:3-adenin-9-yl-2-hydroxypropanoic acid; D000225:Adenine; C079308:6-chloropurine