The biological activity of tetrakis(benzoxazine) calix[4]resorcinarenes and as a host for small molecules

IF 1.6 4区化学 Q2 Agricultural and Biological Sciences

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2025-02-01 DOI:10.1007/s10847-025-01278-0

Jing-Long Liu, Xiao-Dan Ye, Lu-Si Chen, Ai-Quan Jia, Qian-Feng Zhang

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Abstract

New ten tetrakis(benzoxazine) calix[4]resorcinarenes modified by organic amine through Mannich reaction were obtained in this paper. Compounds 2 ~ 11 were characterized by infrared spectroscopies, nuclear magnetic resonance spectroscopies. The structure of compounds 2, 10 and 11 was characterized by single crystal X-ray diffraction. Compound 7 possesses a MIC value of 3.13 μg/mL against S. Aureus, demonstrating a favorable inhibitory effect, and a MIC value of 6.25 μg/mL against E. Coli, likewise showing a good inhibitory effect. The UV and ¹H NMR titration experiments were conducted to explore the host–guest chemistry between compound 10 and acetonitrile molecules, indicating that compound 10 exhibited encapsulation behavior towards acetonitrile molecules through hydrogen bonding interactions. Then Hirshfeld surface analysis showed that H⋅⋅⋅H, C − H⋅⋅⋅O, C − H⋅⋅⋅π, O − H⋅⋅⋅O played an important role in the crystal accumulation of compounds 2, 10 and 11.

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四（苯并恶嗪）杯状间苯二甲酸酯的生物活性及其作为小分子宿主的作用

采用曼尼希反应对有机胺进行了改性，得到了新的十四（苯并恶嗪）杯状间苯二甲酸酯。化合物2 ~ 11通过红外光谱、核磁共振光谱进行了表征。化合物2、10和11的结构通过单晶x射线衍射进行了表征。化合物7对金黄色葡萄球菌的MIC值为3.13 μg/mL，表现出良好的抑制效果；对大肠杆菌的MIC值为6.25 μg/mL，同样表现出良好的抑制效果。通过紫外和1H NMR滴定实验探讨了化合物10与乙腈分子之间的主客体化学关系，发现化合物10通过氢键相互作用对乙腈分子表现出包封行为。Hirshfeld表面分析表明，H⋅⋅H、C−H⋅⋅O、C−H⋅⋅⋅π、O−H⋅⋅⋅O对化合物2、10和11的结晶积累起重要作用。

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry 化学-化学综合

CiteScore

3.30

自引率

8.70%

发文量

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.