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Discovery of (R)-2-Amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic Acid and Congeners As Highly Potent Inhibitors of Human Arginases I and II for Treatment of Myocardial Reperfusion Injury

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    Discovery of (R)-2-Amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic Acid and Congeners As Highly Potent Inhibitors of Human Arginases I and II for Treatment of Myocardial Reperfusion Injury
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    † The Institutes for Pharmaceutical Discovery, LLC, 23 Business Park Drive, Branford, Connecticut 06405, United States
    ‡ Department of Integrative Biology, IGBMC, CNRS, INSERM, Université de Strasbourg, 1 rue Laurent Fries, 67404 Illkirch, France
    § IFLYSIB, Conicet, UNLP, Calle 59 N° 789, La Plata, Argentina
    ∥ Mars, Incorporated, 6885 Elm Street, McLean,Virginia 22101, United States
    *Phone: 203-494-1672. E-mail: [email protected]
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2013, 56, 6, 2568–2580
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    https://doi.org/10.1021/jm400014c
    Published March 8, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    Recent efforts to identify treatments for myocardial ischemia reperfusion injury have resulted in the discovery of a novel series of highly potent α,α-disubstituted amino acid-based arginase inhibitors. The lead candidate, (R)-2-amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic acid, compound 9, inhibits human arginases I and II with IC50s of 223 and 509 nM, respectively, and is active in a recombinant cellular assay overexpressing human arginase I (CHO cells). It is 28% orally bioavailable and significantly reduces the infarct size in a rat model of myocardial ischemia/reperfusion injury. Herein, we report the design, synthesis, and structure–activity relationships (SAR) for this novel series of inhibitors along with pharmacokinetic and in vivo efficacy data for compound 9 and X-ray crystallography data for selected lead compounds cocrystallized with arginases I and II.

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    1H NMR and 13C NMR spectra, LC MS/MS data, analytical HPLC chromatograms, chiral HPLC chromatograms, and X-ray crystallography data collection and refinement statistics. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Med. Chem. 2013, 56, 6, 2568–2580
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    Published March 8, 2013
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