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    Configurational stability of bisindolylmaleimide cyclophanes: from conformers to the first configurationally stable, atropisomeric bisindolylmaleimides.

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    URI
    http://hdl.handle.net/11287/619058
    Author
    Barrett, S.
    Bartlett, S.
    Bolt, Amanda H.
    Ironmonger, A.
    Joce, C.
    Nelson, A.
    Woodhall, T.
    Date
    2005-10-21
    Journal
    Chemistry (Weinheim an der Bergstrasse, Germany)
    Type
    Research Support, Non-U.S. Gov't
    Publisher
    Wiley
    DOI
    10.1002/chem.200500520
    Rights
    Archived with thanks to Chemistry (Weinheim an der Bergstrasse, Germany)
    Metadata
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    Abstract
    The bisindolylmaleimides are selective protein kinase inhibitors that can adopt two limiting diastereomeric (syn and anti) conformations. The configurational stability of a range of substituted and macrocyclic bisindolylmaleimides was investigated by using appropriate techniques. With unconstrained bisindolylmaleimides, the size of the 2-indolyl substituents was found to affect configurational stability, though not sufficiently to allow atropisomeric bisindolylmaleimides to be obtained. However, with a tether between the two indole nitrogen atoms in place, the steric effect of 2-indolyl substituents was greatly exaggerated, leading to large differences in configurational stability. The rate of interconversion of the syn and anti conformers varied by over twenty orders of magnitude through substitution of a bisindolylmaleimide ring system, which was constrained within a macrocyclic ring. Indeed, the first examples of configurationally stable atropisomeric bisindolylmaleimides are reported; the half-life for epimerisation of these compounds at room temperature was estimated to be >10(7) years.
    Citation
    Configurational stability of bisindolylmaleimide cyclophanes: from conformers to the first configurationally stable, atropisomeric bisindolylmaleimides. 2005, 11 (21):6277-85 Chemistry
    Publisher URL
    http://onlinelibrary.wiley.com/doi/10.1002/chem.200500520/full?scrollTo=references
    Note
    This article is freely available via Open Access. Click on the 'Additional Link' above to access the full-text from the publisher's site.
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