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Fluorinated Isatin Derivatives. Part 2. New N-Substituted 5-Pyrrolidinylsulfonyl Isatins as Potential Tools for Molecular Imaging of Caspases in Apoptosis

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    Fluorinated Isatin Derivatives. Part 2. New N-Substituted 5-Pyrrolidinylsulfonyl Isatins as Potential Tools for Molecular Imaging of Caspases in Apoptosis
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    Organisch-Chemisches Institut and International NRW Graduate School of Chemistry, Westfälische Wilhelms-Universität, Corrensstrasse 40, D-48149 Münster, Germany, Klinik und Poliklinik für Nuklearmedizin, Universitätsklinikum Münster, Albert-Schweitzer-Strasse 33, D-48129 Münster, Germany, European Institute of Molecular Imaging, Westfälische Wilhelms-Universität, Mendelstrasse 11, D-48149 Münster
    * To whom correspondence should be addressed. Phone: +49-(0)251-83 33281. Fax: +49-(0)251-83 39772. E-mail: [email protected]
    †Organisch-Chemisches Institut and International NRW Graduate School of Chemistry, Westfälische Wilhelms-Universität.
    ‡Klinik und Poliklinik für Nuklearmedizin, Universitätsklinikum Münster.
    §European Institute of Molecular Imaging, Westfälische Wilhelms-Universität.
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2009, 52, 11, 3484–3495
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    https://doi.org/10.1021/jm8015014
    Published May 15, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    Caspases are responsible for the execution of the cell death program and are potentially suitable targets for the specific imaging of apoptosis in vivo. A series of N-1-substituted analogues of the small molecule nonpeptide caspase inhibitor (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (1), which may be useful for the development of caspase-targeted radioligands, were synthesized and their inhibition potencies were evaluated in vitro. Two of the most powerful techniques to introduce fluorine into organic compounds, viz, bromofluorination of olefins and fluorohydrin synthesis by ring-opening of epoxides, were used. Most of the target compounds are potent inhibitors of the two effector caspases-3 and -7. Furthermore, the 18F-radiolabeled model compound (S)-1-[4-(1-[18F]fluoro-2-hydroxyethyl)benzyl]-5-[1-(2-methoxymethyl-pyrrolidinyl)sulfonyl]isatin ([18F]37), a putative tracer for the noninvasive imaging of apoptosis by positron emission tomography (PET) was synthesized by nucleophilic epoxide ring-opening of its precursor 36. The radiochemistry utilized in the 18F-fluorination reverted to carrier-added [18F]Et3N·3HF, a new fluorine-18 source for radiolabeling.

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    Experimental procedures and spectroscopic data of starting materials and assignment of spectroscopic data of all synthesized compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2009, 52, 11, 3484–3495
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm8015014
    Published May 15, 2009
    Copyright © 2009 American Chemical Society
    Request reuse permissions

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