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J Med Chem. 2011 Sep 22;54(18):6399-403. doi: 10.1021/jm200411j. Epub 2011 Aug 22.

Improved synthesis of chiral pyrrolidine inhibitors and their binding properties to neuronal nitric oxide synthase.

Author information

1
Departments of Chemistry and Molecular Biosciences, Chemistry of Life Processes Institute, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, Illinois 60208-3113, USA.

Abstract

We report an efficient synthetic route to chiral pyrrolidine inhibitors of neuronal nitric oxide synthase (nNOS) and crystal structures of the inhibitors bound to nNOS and to endothelial NOS. The new route enables versatile structure-activity relationship studies on the pyrrolidine-based scaffold, which can be beneficial for further development of nNOS inhibitors. The X-ray crystal structures of five new fluorine-containing inhibitors bound to nNOS provide insights into the effect of the fluorine atoms on binding.

PMID:
21809851
PMCID:
PMC3174355
DOI:
10.1021/jm200411j
[Indexed for MEDLINE]
Free PMC Article

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