Journal of Medicinal Chemistry p. 1833 - 1839 (1990)
Update date:2022-08-05
Topics:
Aerschot, Arthur Van
Everaert, Dirk
Balzarini, Jan
Augustyns, Koen
Jie, Liu
at al.
In view of the selective anti-HIV activity of 2',3'-dideoxy-3'-fluoro-5-chlorouridine (11), a series of eight 2',3'-dideoxy-5-chloropyrimidines were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus type 1 (HIV-1) replication in MT-4 cells.A marked improvement in selectivity was noted for the 5-chlorouracil derivatives of 2,3-dideoxyribofuranose, 3-azido-2,3-dideoxyribofuranose, and 3-fluoro-2,3-dideoxyribofuranose, mainly due to decreased toxicity of the compounds for the host cells.While chlorination of 2',3'-dideoxycytidine remo ved the anti-HIV activity, introduction of chlorine at the C-5 position of 3'-fluoro-, 3'-azido- or 2',3'-didehydro-2',3'-dideoxycytidine led to reduced cytotoxicity with only slightly reduced anti-HIV activity.X-ray analysis showed compound 11 to have two molecules in the asymmetric unit with κ = -168.8(3) deg and -131.3(3) deg and P = 179(1) deg and 163(1) deg, respectively; thus revealing no close resemblance to 3'-azido-3'-deoxythymidine (AZT).
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