Nucleosides and Nucleotides p. 459 - 479 (1994)
Update date:2022-08-05
Topics:
Kasnar
Wise
Kucera
Drach
Townsend
The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3- dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-β-D- erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-β-D- erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.
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Doi:10.1021/ja504835a
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(1994)