在温和条件下高效固相合成具有两个多样化位点的3-取代-5-氧代-5H-噻唑并[2,3-b]喹唑啉-8-甲酰胺。
Efficient solid-phase synthesis of 3-substituted-5-oxo-5H-thiazolo[2,3-b]-quinazoline-8-carboxamides under mild conditions with two diversity positions.
作者信息
Bouillon Isabelle, Krchnák Viktor
机构信息
Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
出版信息
J Comb Chem. 2007 Nov-Dec;9(6):912-5. doi: 10.1021/cc700122a. Epub 2007 Oct 2.
Abstract
Highly efficient solid-phase synthesis of thiazolo[2,3,b]quinazolines under mild conditions was developed using resin-bound 2-amino-terephthalamic acid, Fmoc-NCS, and bromoketones. Primary amines immobilized to an acid-cleavable backbone amide linker were acylated with 1-methyl-2-aminoterephtalate. Following cleavage of the methyl ester, Fmoc-NCS was used to form a resin-bound thiourea. Bromoketones were subsequently added to form an aminothiazole ring and the cyclization was performed using DIC/HOBt to afford thiazolo[2,3,b]quinazolines. Highly efficient solid-phase synthesis is amenable to high throughput/combinatorial synthesis.
摘要
使用树脂结合的2-氨基对苯二甲酸、Fmoc-NCS和溴代酮，在温和条件下开发了噻唑并[2,3,b]喹唑啉的高效固相合成方法。固定在酸可裂解主链酰胺连接基上的伯胺用1-甲基-2-氨基对苯二甲酸酯进行酰化。甲酯裂解后，用Fmoc-NCS形成树脂结合的硫脲。随后加入溴代酮形成氨基噻唑环，并使用DIC/HOBt进行环化反应，得到噻唑并[2,3,b]喹唑啉。高效固相合成适用于高通量/组合合成。
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