Journal of Medicinal Chemistry p. 1351 - 1355 (1988)
Update date:2022-08-02
Topics:
Boryski, Jerzy
Golankiewicz, Bozenna
Clercq, Erik De
Novel N-substituted derivatives of acyclovir (1a) were synthesized and evaluated for their antiviral, antimetabolic, and antitumor cell properties in vitro.Monomethylation of 1a at positions 1, 7, and N-2 gave compounds 2-4, respectively.When positions 1 and N-2 were linked together by an isopreno group, the tricyclic 9-<(2-hydroxyethoxy)methyl>-1,N-2-isopropenoquanine (5) was obtained.Compound 5 was then further methylated at positions N-2 and 7 to give 6 and 7, respectively.None of the new acyclovir derivatives showed any appreciable antimetabolic or antitumor cell activity.However, compounds 2 and 5 exhibited a marked antiherpetic activity.Their activity spectrum was similar to that of acyclovir, and their selectivity as inhibitors of herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) was at least as great as, if not greater than, that of acylclovir.
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