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

Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic alpha-helical mimics.
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轻松迭代合成 2,5-三联嘧啶亚基作为非肽 α 螺旋模拟物。

DOI:
10.1021/jo100272d
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发表时间:
2010
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
McLaughlin,MarkL
McLaughlin,MarkL
中科院分区:
--
文献类型:
--
作者:
Anderson,Laura;Zhou,Mingzhou;Sharma,Vasudha;McLaughlin,JillianM;Santiago,DanielN;Fronczek,FrankR;Guida,WayneC;McLaughlin,MarkL

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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 thei,i+ 4, andi+ 7 sites of an α-helix.