一种新型手性大环二内酰胺的设计合成及其核磁共振和单晶x射线衍射表征

IF 1.6 4区 化学 Q2 Agricultural and Biological Sciences
Divina P. Sanchez-Perez, Victor Gómez-Calvario, Jacqueline Jiménez, Manuel Velasco, Angel Mendoza, Jorge R. Juárez
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引用次数: 0

摘要

在这项研究中,我们报道了一种新的手性大环双内酰胺(1)的合成和结构表征,该化合物以(R)-苯基甘二醇为关键构建块。大环聚醚双酰胺,如这种化合物,因其与阳离子、阴离子、重金属离子和中性有机分子形成配合物的能力而引起了人们的关注,显示出作为分子或离子受体和抗生素的潜在生物学应用。基于我们在合成手性哌啶衍生物用于生物碱合成方面的专业知识,我们采用了高效的非对映选择策略来开发这个大环。通过二维核磁共振波谱和x射线衍射分析,完成了完整的结构分配,这对于将结构模式与生物活性相关联至关重要。这项工作为在超分子体系和药物化学中具有潜在应用价值的双氮冠醚的设计提供了有价值的见解。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Design and synthesis of a new chiral macrocyclic dilactam and its characterization by NMR and single-crystal X-ray diffraction

In this study, we report the synthesis and structural characterization of a new chiral macrocyclic dilactam (1) using (R)-phenylglycinol as a key building block. Macrocyclic polyether dilactams, such as this compound, have garnered attention for their ability to form complexes with cations, anions, heavy-metal ions, and neutral organic molecules, displaying potential biological applications as molecular or ion receptors and antibiotics. Building on our expertise in synthesizing chiral piperidine derivatives for alkaloid synthesis, we employed efficient diastereoselective strategies to develop this macrocycle. The complete structural assignment, crucial for correlating structural patterns with biological activity, was achieved through two-dimensional NMR spectroscopy and X-ray diffraction analysis. This work provides valuable insights into the design of diaza-crown ethers with potential applications in supramolecular systems and medicinal chemistry.

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来源期刊
CiteScore
3.30
自引率
8.70%
发文量
0
审稿时长
3-8 weeks
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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