Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic alpha-helical mimics.

Autor: Anderson L; Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE 205, Tampa, Florida 33620, USA., Zhou M, Sharma V, McLaughlin JM, Santiago DN, Fronczek FR, Guida WC, McLaughlin ML
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2010 Jun 18; Vol. 75 (12), pp. 4288-91.
DOI: 10.1021/jo100272d
Abstrakt: A facile iterative synthesis of 2,5-terpyrimidinylenes that are structurally analogous to alpha-helix mimics is presented. Condensation of amidines with readily prepared alpha,beta-unsaturated alpha-cyanoketones gives 5-cyano-substituted pyrimidines. Iterative transformation of the 5-cyano group into an amidine allows synthesis of 2,5-terpyrimidinylenes with variable groups at the 4-, 4'-, and 4''-positions. These compounds are designed to mimic the i, i + 4, and i + 7 sites of an alpha-helix.
Databáze: MEDLINE