作为非肽类α-螺旋模拟物的 2,5-嘧啶二烯的简便迭代合成。
Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic alpha-helical mimics.
机构信息
Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE 205, Tampa, Florida 33620, USA.
出版信息
J Org Chem. 2010 Jun 18;75(12):4288-91. doi: 10.1021/jo100272d.
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.
摘要
本文提出了一种简便的 2,5-嘧啶二烯类似物的迭代合成方法，这些化合物结构类似于α-螺旋模拟物。将脒与易于制备的α,β-不饱和α-氰基酮缩合得到 5-氰基取代的嘧啶。将 5-氰基基团反复转化为脒，可在 4-、4' -和 4'' -位合成具有可变取代基的 2,5-嘧啶二烯。这些化合物旨在模拟α-螺旋的 i、i+4 和 i+7 位。
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