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

ABSTRACT: 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.

SUBMITTER: Anderson L

PROVIDER: S-EPMC2901110 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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

Anderson Laura L 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

The Journal of organic chemistry 20100601 12

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. ...[more]

PMID: 20469918

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