Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76016, USA.
Institut des Sciences Analytiques, CNRS, University of Lyon, 5 rue de la Doua, 69100 Villeurbanne, France.
Molecules. 2021 Jan 4;26(1):213. doi: 10.3390/molecules26010213.
Twelve new azole compounds were synthesized through an ene reaction involving methylidene heterocycles and phenylmaleimide, producing four oxazoles, five thiazoles, and one pyridine derivative, and ethyl glyoxal for an oxazole and a thiazole compound. The twelve azoles have a stereogenic center in their structure. Hence, a method to separate the enantiomeric pairs, must be provided if any further study of chemical and pharmacological importance of these compounds is to be accomplished. Six chiral stationary phases were assayed: four were based on macrocyclic glycopeptide selectors and two on linear carbohydrates, i.e., derivatized maltodextrin and amylose. The enantiomers of the entire set of new chiral azole compounds were separated using the three different mobile phase elution modes: normal phase, polar organic, and reversed phase. The most effective chiral stationary phase was the MaltoShell column, which was able to separate ten of the twelve compounds in one elution mode or another. Structural similarities in the newly synthesized oxazoles provided some insights into possible chiral recognition mechanisms.
通过涉及亚甲基杂环和苯马来酰亚胺的烯反应，合成了 12 种新的唑类化合物，生成了 4 个噁唑、5 个噻唑和 1 个吡啶衍生物，以及 1 个噁唑和 1 个噻唑化合物的乙基乙二醛。这 12 种唑类化合物在其结构中具有一个手性中心。因此，如果要完成这些化合物的化学和药理学重要性的进一步研究，就必须提供一种分离对映体的方法。我们测试了 6 种手性固定相：4 种基于大环糖肽选择器，2 种基于线性碳水化合物，即衍生化的麦芽糊精和直链淀粉。使用三种不同的流动相洗脱模式：正相、极性有机相和反相，分离了整套新的手性唑类化合物的对映体。最有效的手性固定相是 MaltoShell 柱，它能够以一种或另一种洗脱模式分离 12 种化合物中的 10 种。新合成的噁唑类化合物的结构相似性为可能的手性识别机制提供了一些见解。
