Synthesis and Conformational Characterization of Diketopiperazines Bearing a Benzyl Moiety

DOI PDF 3 Citations 24 References
  • Nakao Michiyasu
    Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Toriuchi Yuriko
    Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Fukayama Shintaro
    Graduate School of Pharmaceutical Sciences, The University of Tokushima
  • Sano Shigeki
    Graduate School of Pharmaceutical Sciences, The University of Tokushima

Description

Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1H NMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1H NMR spectra. An intramolecular CH–π interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group.

Journal

  • Chemistry Letters

    Chemistry Letters 43 (3), 340-342, 2014

    The Chemical Society of Japan

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