Journal of Medicinal Chemistry p. 1045 - 1050 (1982)
Update date:2022-09-26
Topics:
Temple, Carroll
Wheeler, Glynn P.
Elliott, Robert D.
Rose, Jerry D.
Kussner, Conrad L.
et al.
Reaction of α-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-<(2-oxo-2-phenylethyl)amino>pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4).Related pyridines substituted with keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4-<<3-(N-methyl-N-phenylamino)-2-hydroxypropyl>amino>-5-nitropyridine-7-carbamates (6).Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7).Several of the oximes 3 were successfully hydrogenated to give 7 directly.The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice.THese biological activities are attributed to the accumulation of cells at mitosis.
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