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J Gen Virol 67 (1986), 1625-1632; DOI 10.1099/0022-1317-67-8-1625
© 1986 Society for General Microbiology
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Structure-Activity Relationships among {alpha}-(N)-Heterocyclic Acyl Thiosemicarbazones and Related Compounds as Inhibitors of Herpes Simplex Virus Type 1-specified Ribonucleoside Diphosphate Reductase

Steven R. Turk1,2,, Charles Shipman, Jr2 and John C. Drach2

1 Interdepartmental Graduate Program in Medicinal Chemistry
and2 Department of Oral Biology, School of Dentistry, The University of Michigan, Ann Arbor, Michigan 48109, U.S.A.

2-Acetylpyridine thiosemicarbazone, a potent antiviral drug, and 13 analogues were examined as inhibitors of partially purified herpes simplex virus type 1-specified ribonucleoside diphosphate reductase. N4,N4-Azacycloheptane derivatives were more active than their N4-unsubstituted analogues. Selenosemicarbazones were similar in potency to their thiosemicarbazone congeners, whereas a related semicarbazone was much less active. Maximum inhibition was observed when an ethylidene side-chain was present in the compounds. No discernible trend in potency was observed when the pyridine moiety was replaced by quinoline or isoquinoline. Thiosemicarbazide derivatives were less potent than their unsaturated thiosemicarbazone analogues. Inhibitory potencies increased at longer incubation times consistent with the hypothesis that thiosemicarbazones inactivate the enzyme in a time-dependent manner.

Keywords: HSV-1, ribonucleotide reductase, antiviral compounds

Received 2 December 1985; accepted 28 April 1986.




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Copyright © 1986 by the Society for General Microbiology.