Collect. Czech. Chem. Commun. 2006, 71, 77-90

Tricyclic Purine Analogs Derived from 2-Amino-6-chloropurine and 2,6-Diaminopurine and Their Methylated Quaternary Salts

Kateřina Hořejší, Radek Pohl and Antonín Holý*

Institute of Organic Chemistry and Biochemistry, Centre for New Antivirals and Antineoplastics, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


A novel series of tricyclic, etheno-bridged purine analogs was sythesized from 2-amino-6-(substituted amino)-9-methylpurines by cyclization with chloroacetaldehyde, with particular focus on the regioselectivity of the cyclization reaction and fluorescence properties. The analogs as well as the starting purines were alkylated with iodomethane, affording a new class of quaternary salts with potential biological activity. Neither significant fluorescence nor cytostatic effect was found.

Keywords: Purines; Alkylation; Chloroacetaldehyde; Fluorescence; Fused heterocycles; Quaternization; Nucleobases.

References: 24 live references.