Structural elucidation of liquid pharmaceutical compounds by porous organic crystals of adamantane-containing macrocycles

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-09-12 DOI:10.1016/j.tet.2025.134939

Tadashi Hyodo , Miku Sugimoto , Masatoshi Kawahata , Masahide Tominaga , Kentaro Yamaguchi

引用次数: 0

Abstract

Two adamantane-containing macrocycles having halobenzene and tetrazine parts were employed as porous host materials in the crystalline sponge method for the structural elucidation of liquid pharmaceutical compounds. The macrocycles were arranged into molecular networks composed of tubular assemblies having one-dimensional pores. Soaking of the porous crystals in methyl salicylate or eugenol afforded the adsorbed crystals in a single-crystal to single-crystal fashion. X-ray analysis revealed that the conformation and packing of the macrocycles in the porous crystals were changed compared with those in the original crystals. Similarly, 4-methylpyrazole (also known as fomepizole) or 3-methylpyrazole were captured within the macrocycle-based organic frameworks, and their molecular structures were confirmed. Remarkably, dimeric structures of the pyrazole derivatives were formed within the macrocycles through hydrogen bonds.

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用含金刚烷大环的多孔有机晶体解析液体药物化合物的结构

在结晶海绵法中，采用两种含有卤苯和四嗪部分的含金刚烷大环作为多孔主体材料，用于液体药物化合物的结构解析。大环被排列成由具有一维孔的管状组件组成的分子网络。将多孔晶体浸泡在水杨酸甲酯或丁香酚中，使所吸附的晶体以单晶到单晶的形式存在。x射线分析表明，与原始晶体相比，多孔晶体中大环的构象和排列发生了变化。同样，在基于大环的有机框架中捕获了4-甲基吡唑（也称为甲吡唑）或3-甲基吡唑，并确定了它们的分子结构。值得注意的是，吡唑衍生物通过氢键在大环内形成二聚体结构。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.