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N-substituted homopiperazine barbiturates as gelatinase inhibitors.

Abstract：

:Matrix metalloproteinases are implicated in a wide range of pathophysiological processes and potent selective inhibitors for these enzymes continue to be eagerly sought. 5,5-Disubstituted barbiturates hold promise as inhibitor types being stable in vivo and relatively selective for the gelatinases (MMP-2 and MMP-9). In this paper we describe the synthesis of 5-piperazine and -homopiperazine substituted barbiturates. The activity of these compounds as gelatinase inhibitors was evaluated using supernatants from 12-O-tetradecanoylphorbol-13-acetate (PMA)-stimulated HT-1080 cells as well as using recombinant human MMPs. N-Acyl homopiperazine compounds were found to be potent inhibitors of the gelatinases (range in nM) and generally more potent than the corresponding piperazine analogues. The panel of N-acyl homopiperazines was enlarged in order to exploit differences between the gelatinases at the S2' site in order to design MMP-2- or MMP-9-selective inhibitors. Compounds in this group exhibited single digit nano-molar potency and some selectivity between the two enzymes. Representative potent compounds were effective inhibitors of cancer cell migration.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Wang J,Medina C,Radomski MW,Gilmer JF

doi

10.1016/j.bmc.2011.06.055

subject

Has Abstract

pub_date

2011-08-15 00:00:00

pages

4985-99

issue

16

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(11)00495-0

journal_volume

19

pub_type

杂志文章

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