TY - JOUR
T1 - Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic α-helical mimics
AU - Anderson, Laura
AU - Zhou, Mingzhou
AU - Sharma, Vasudha
AU - McLaughlin, Jillian M.
AU - Santiago, Daniel N.
AU - Fronczek, Frank R.
AU - Guida, Wayne C.
AU - McLaughlin, Mark L.
PY - 2010/6/18
Y1 - 2010/6/18
N2 - A facile iterative synthesis of 2,5-terpyrimidinylenes that are structurally analogous to α-helix mimics is presented. Condensation of amidines with readily prepared α,β-unsaturated α-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 α-helix.
AB - A facile iterative synthesis of 2,5-terpyrimidinylenes that are structurally analogous to α-helix mimics is presented. Condensation of amidines with readily prepared α,β-unsaturated α-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 α-helix.
UR - http://www.scopus.com/inward/record.url?scp=77953522406&partnerID=8YFLogxK
U2 - 10.1021/jo100272d
DO - 10.1021/jo100272d
M3 - Article
C2 - 20469918
AN - SCOPUS:77953522406
SN - 0022-3263
VL - 75
SP - 4288
EP - 4291
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 12
ER -