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静态组合化学：一种用于大环苯甲酰胺文库合成的高压方法。

Static Combinatorial Chemistry: A High-Pressure Approach to the Synthesis of Macrocyclic Benzoamide Libraries.

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

出版信息

ACS Comb Sci. 2020 Apr 13;22(4):213-221. doi: 10.1021/acscombsci.0c00024. Epub 2020 Mar 20.

DOI:10.1021/acscombsci.0c00024
PMID:32163264
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7588042/
Abstract

We investigated the yield and distribution of macrocyclic products formed in combinatorial libraries (CLs) obtained via double-amidation reactions of methyl diesters with α,ω-diamines. The application of the static combinatorial chemistry (SCC) approach allowed us to generate a large number of macrocyclic diamides and tetraamides in single experiments. We show that high-pressure conditions accelerate the macrocyclization process but also have a great impact on the distribution of macrocyclic products in the presented libraries, promoting the formation of macrocyclic compounds and eliminating the linear ones. The distribution of macrocyclic products was also found to be strongly dependent on the structural features of the substrates employed. Furthermore, in three- and four-substrate CLs we observed the formation of a new type of hybrid tetraamides consisting of three different components.

摘要

我们研究了通过甲酯与 ω-二胺的双重酰胺化反应得到的组合文库 (CL) 中形成的大环产物的产率和分布。静态组合化学 (SCC) 方法的应用使我们能够在单次实验中生成大量的大环二酰胺和四酰胺。我们表明，高压条件不仅可以加速大环化过程，还会对所研究的文库中大环产物的分布产生重大影响，促进大环化合物的形成并消除线性产物。大环产物的分布也被发现强烈依赖于所使用的底物的结构特征。此外，在三底物和四底物 CL 中，我们观察到由三个不同成分组成的新型杂四酰胺的形成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77cb/7588042/38e4082f0851/co0c00024_0007.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77cb/7588042/38e4082f0851/co0c00024_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77cb/7588042/60135bbca109/co0c00024_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77cb/7588042/9386a0419f1e/co0c00024_0008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77cb/7588042/38e4082f0851/co0c00024_0007.jpg

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