Bioorganic and Medicinal Chemistry Letters p. 1601 - 1606 (1996)
Update date:2022-08-04
Topics: Synthesis Optimization In Vivo Testing Publication and Reporting Patent and Regulatory Considerations Rational Design Biological Activity Testing Toxicity and ADME Profiling Structure Determination
Chen, Jian Jeffrey
Zhang, Yiping
Hammond, Scott
Dewdney, Nolan
Ho, Teresa
Lin, Xiaohong
Browner, Michelle F.
Castelhano, Arlindo L.
A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP- 7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere.
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