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Quantitative structure-activity relationships of N2-phenylguanines as inhibitors of herpes simplex virus thymidine kinases.

Abstract：

:Quantitative structure-activity relationships of the Hansch-type were developed to account for inhibition of thymidine kinases from Herpes simplex viruses types 1 and 2 (HSV1,2) by N2-phenylguanines. Derivatives with meta and/or para substituents on the phenyl ring display a wide range of overlapping, but not identical, potencies as inhibitors of the enzymes. IC50 values for 36 (HSV1) and 35 inhibitors (HSV2) were used to develop equations using hydrophobic (pi), electronic (sigma, R), and group size (MR) parameters. Equations 1 and 2 with correlation coefficients of 0.797 and 0.805, respectively, were obtained for inhibitors of the types 1 and 2 enzymes. Potencies were correlated positively with pi values of meta substituents but negatively with pi values of para substituents in the phenyl ring. Positive correlations were also obtained with the resonance parameter R of para substituents and with sigma constants of meta substituents. The most potent inhibitor of both enzymes was N2-[m-(trifluoromethyl)phenyl]guanine, although HSV2 thymidine kinase was more sensitive to certain compounds than the HSV1 enzyme.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Gambino J,Focher F,Hildebrand C,Maga G,Noonan T,Spadari S,Wright G

doi

10.1021/jm00094a007

keywords:

subject

Has Abstract

pub_date

1992-08-07 00:00:00

pages

2979-83

issue

16

eissn

0022-2623

issn

1520-4804

journal_volume

35

pub_type

杂志文章

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