Charting the Chemical Reaction Space around a Multicomponent Combination: Controlled Access to a Diverse Set of Biologically Relevant Scaffolds
Charting the Chemical Reaction Space around a Multicomponent Combination: Controlled Access to a Diverse Set of Biologically Relevant Scaffolds
复制标题
绘制围绕多组分组合的化学反应空间：对一组不同的生物相关支架的受控访问
DOI：
10.1002/ange.202303889
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发表时间：
2023
影响因子：
--
通讯作者：
Nadal Rodríguez P
中科院分区：
文献类型：
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作者：
Nadal Rodríguez P
绘制周围的羰基化合物，胺，和异氰乙酸酯的组合的化学反应空间允许新的多组分过程的描述，导致各种不饱和的咪唑啉酮支架。所得化合物显示出绿色荧光蛋白的发色团和天然产物腔肠素的核心。尽管所涉及的途径具有竞争性，但一般方案提供了对所需化学型的选择性访问。此外，我们描述了在咪唑酮核心的C-2位置处的前所未有的反应性，以直接提供具有天然产物（例如亮氨酸胺）、有效激酶抑制剂和具有合适光学和生物学特性的荧光探针的C、S和N-衍生物。
Charting the chemical reaction space around the combination of carbonyls, amines, and isocyanoacetates allows the description of new multicomponent processes leading to a variety of unsaturated imidazolone scaffolds. The resulting compounds display the chromophore of the green fluorescent protein and the core of the natural product coelenterazine. Despite the competitive nature of the pathways involved, general protocols provide selective access to the desired chemotypes. Moreover, we describe unprecedented reactivity at the C‐2 position of the imidazolone core to directly afford C, S, and N‐derivatives featuring natural products (e.g. leucettamines), potent kinase inhibitors, and fluorescent probes with suitable optical and biological profiles.