Journal of Medicinal Chemistry p. 423 - 427 (1985)
Update date:2022-08-02
Topics:
Patil, Vemanna D.
Wise, Dean S.
Wotring, Linda L.
Bloomer, Linda C.
Townsend, Leroy B.
The title nucleoside 5 was prepared by a condensation of the silylated heterocycle thieno<2,3-d>pyrimidin-4-one (1) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (2a) in the presence of a Lewis acid or with 2,3,5-tri-O-acetyl-D-ribofuranosyl bromide (2b) in the presence of mercuric oxide and mercuric bromide.The site of ribosylation and anomeric configuration of this nucleoside were established by 1H NMR.The synthesis of 3-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidin-4-one (8), 1-phenyl-5-β-D-ribofuranosylpyrazolo<3,4-d>pyrimidin-4-one (9), 5-methyl-3-β-D-ribofuranosylthieno<2,3-d>pyrimidin-4-one (10), and 2-methyl-6-β-D-ribofu ranosyltriazolo<5,4-d>pyrimidin-7-one (11) is also described.The title compound inhibited the growth of murine L-1210 leukemic cells in vitro with and ID50 of 3*10-5 M.The growth inhibition could not be prevented bu uridine, cytidine, thymidine, deoxycytidine, cytosine, hypoxanthine, or uridine and hypoxanthine together.On the other hand, inhibition of adenosine kinase by 10-7 M 5-iodotubercidin prevented the cytotoxic effect.Also a subline of L-1210 cells resistant to several cytotoxic adenosine analogues was also resistant to this nucleoside.Thus it appears that this compound 5 may act as an adenosine analogue
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