Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4-one (2'-deoxy-9-deazaguanosine).
A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'-deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4-one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento-furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.
Gibson
E S
ES
Graduate School of Medical Sciences, Department of Pharmacology, Cornell University, New York, NY 10021, USA.
Lesiak
K
K
Watanabe
K A
KA
Gudas
L J
LJ
Pankiewicz
K W
KW
D000818:Animals; D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D004354:Drug Screening Assays, Antitumor; D007202:Indicators and Reagents; D007939:Leukemia L1210; D016399:Lymphoma, T-Cell; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D014407:Tumor Cells, Cultured
C119904:2'-deoxy-9-deazaguanosine; D000964:Antimetabolites, Antineoplastic; D007202:Indicators and Reagents; D003849:Deoxyguanosine