Synthesis of the phenylpyridal scaffold as a helical peptide mimetic.

ABSTRACT: Phenylpyridal- and phenyldipyridal-based scaffolds have been designed and synthesized as novel helical peptide mimetics. The synthesis required optimisation and selective alkylation in producing 2,6-functionalized 3-hydroxypyridine derivatives for a convergent scheme. The pyridine analogues were coupled by a series of Suzuki/Stille types cross-coupling reactions. A series of biaryl and ter-aryl substituted heterocycles were produced. The synthetic approach was concise and high yielding allowing large variability at the wanted side-chain attachment points. A number of compounds were synthesised to show the versatility of the strategy.

SUBMITTER: Bourne GT 

PROVIDER: S-EPMC3531917 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature