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Benzothiadiazine dioxide dibenzyl derivatives as potent human cytomegalovirus inhibitors: synthesis and comparative molecular field analysis.

Abstract：

:The benzothiadiazine dioxide (BTD) derivatives are potent nonnucleoside human cytomegalovirus (HCMV) inhibitors. As part of our comprehensive structure-activity relationship study of these compounds, we have now synthesized N,N- and N,O-dibenzyl derivatives with different para-substituents (alkyl, phenyl, electron-donating, electron-withdrawing) in the phenyl ring of the benzyl moieties. The antiviral activity against HCMV (AD-169 strain) was also experimentally measured showing IC(50) values between 2.5 and 50 microM. Comparative molecular field analysis (CoMFA) was employed to generate a model, based upon 32 diverse BTD derivatives, to delineate structural and electrostatic features important for enhanced activity against HCMV. The steric (van der Waals) interactions with the receptor majoritary describes the variation in antiviral activity among the inhibitors. Finally, the CoMFA model was used to design two sets of novel BTD derivatives. Synthesis and subsequent anti-HCMV evaluation of these compounds enabled us to maintain the activity of this new kind of HCMV inhibitors.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Martinez A,Gil C,Abasolo MI,Castro A,Bruno AM,Perez C,Prieto C,Otero J

doi

10.1021/jm000033p

keywords:

subject

Has Abstract

pub_date

2000-08-24 00:00:00

pages

3218-25

issue

17

eissn

0022-2623

issn

1520-4804

pii

jm000033p

journal_volume

43

pub_type

杂志文章

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