Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic alpha-helical mimics.
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.
Anderson
Laura
L
Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE 205, Tampa, Florida 33620, USA.
Zhou
Mingzhou
M
Sharma
Vasudha
V
McLaughlin
Jillian M
JM
Santiago
Daniel N
DN
Fronczek
Frank R
FR
Guida
Wayne C
WC
McLaughlin
Mark L
ML
D000578:Amidines / Q000737:chemistry*; D032701:Biomimetics; D003489:Cyanoketone / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D017433:Protein Structure, Secondary; D011743:Pyrimidines / Q000737:chemistry*
D000578:Amidines; D011743:Pyrimidines; D003489:Cyanoketone
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