期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 14, 页码 5709-5712出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo050339+
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Matrix metalloproteinases (MMPs), of which 26 are known, have been implicated in a number of pathological conditions, including tumor metastasis. We have previously described the first mechanism-based inhibitor for MMPs (J. Am. Chem. Soc. 2000, 122, 6799-6800), which in chemistry mediated by the active site zinc ion selectively and covalently inhibits MMP-2, -3, and -9. Computational analyses indicated that this selectivity in inhibition of MMPs could be improved by design of new variants of the inhibitor class. We report herein the syntheses of methyl 2-(4-[4-[(2-thiiranylpropyl)sulfonyl]phenoxylphenyl)acetate (3) and 2-(4-{4-[(2-thiiranylpropyl)sulfonyllphenoxylphenyl)acetic acid (4), and show that compound 3 serves as a mechanism-based inhibitor exclusively for MMP-2. This molecule should prove useful in delineating the functions of MMP-2 in biological systems.
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