Collect. Czech. Chem. Commun. 1988, 53, 1779-1794

Fluorescent analogues of acyclic inhibitors of S-adenosyl-L-homocysteine hydrolase

Hana Dvořáková, Antonín Holý and Milena Masojídková

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Condensation of sodium salt of 2-aminopurine (I) with 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (II) followed by acid hydrolysis afforded 9-(RS)-(2,3-dihydroxypropyl)-2-aminopurine (V). Similarly, sodium salt of lin-benzoadenine (IX) reacted with compound II to give 3-(RS)-(2,3-dihydroxypropyl)-lin-benzoadenine (Xb). Analogues of eritadenine (XVIb) derived from 2-aminopurine (VII) and lin-benzoadenine (XIV) were obtained by reaction of sodium salt of the corresponding base (I or IX) with 2,3-O-cyclohexylidene-D-erythronolactone (VI) and subsequent acid hydrolysis. By action of chloroacetaldehyde on 9-substituted acyclic analogues of adenosine or AMP (XVI) were prepared 9-(2,3-dihydroxypropyl)-1,N6-ethenoadenine (XVIIa), 1,N6-etheno derivative of eritadenine (XVIIb), 3-(1,N6-ethenoadenin-9-yl)-2-hydroxypropanoic acid (XVIIc) and its 2-methylpropyl ester (XVIId), as well as 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)-1,N6-ethenoadenine (XVIIe) and 9-(2-phosphonylmethoxyethyl)-1,N6-ethenoadenine (XVIIf). Fluorescence spectra of all the mentioned compounds exhibit parameters corresponding to the substituted fluorophore; however, no pronounced inhibitory effect on SAH-hydrolase from L-1210 mice leukemia cells has been found for any of them.