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Five-membered heterocyclic ureas suitable for the donor–donor–acceptor hydrogen-bonding modules

Tetrahedron Letters, ISSN: 0040-4039, Vol: 49, Issue: 12, Page: 2005-2009
2008
  • 18
    Citations
  • 0
    Usage
  • 13
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    18
    • Citation Indexes
      17
    • Patent Family Citations
      1
      • Patent Families
        1
  • Captures
    13

Article Description

Five-membered heterocyclic ureas are capable of forming the unfolded conformer without preorganization by using the intramolecular hydrogen bond, and are suitable for the DDA hydrogen-bonding modules. In contrast, six-membered heterocyclic ureas are destabilized by an effect of steric repulsion due to the closer distance of CH c ⋯O and their conformational equilibriums are biased toward the stable folded conformer.

Bibliographic Details

Yosuke Hisamatsu; Yuki Fukumi; Naohiro Shirai; Shin-ichi Ikeda; Kazunori Odashima

Elsevier BV

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry

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