Stereospecific synthesis of 5-substituted 2-bisarylthiocyclopentane carboxylic acids as specific matrix metalloproteinase inhibitors.
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Le Diguarher T, Chollet AM, Bertrand M, Hennig P, Raimbaud E, Sabatini M, Guilbaud N, Pierre A, Tucker GC, Casara P
Stereospecific synthesis of 5-substituted 2-bisarylthiocyclopentane carboxylic acids as specific matrix metalloproteinase inhibitors.
J Med Chem. 2003 Aug 28;46(18):3840-52.
- PubMed ID
- 12930146 [ View in PubMed]
- Abstract
The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Marimastat 72 kDa type IV collagenase IC 50 (nM) 1.8 N/A N/A Details Marimastat Collagenase 3 IC 50 (nM) 3.4 N/A N/A Details Marimastat Interstitial collagenase IC 50 (nM) 1.5 N/A N/A Details Marimastat Matrix metalloproteinase-9 IC 50 (nM) 1.6 N/A N/A Details Marimastat Stromelysin-1 IC 50 (nM) 25 N/A N/A Details