Chalcone-Mediated and unexpected rearrangement preparation of 1H-pyrazol-furo[2,3-d]pyrimidine derivatives as potent antitumor agents

IF 4.7 2区化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2025-04-14 DOI:10.1016/j.molstruc.2025.142312

Junkai Ma , Chen Wu , Wenyu Zhao , Fengxu Wu , Lun Luo, Yanggen Hu

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Abstract

The versatility of N-heterocyclic rings is the focus of most attention because of their remarkable biological activities. In this study, a new chalcone-mediated and unexpected rearrangement reaction has been explored for the preparation of 1H-pyrazol-furo[2,3-d]pyrimidines 5a-5r. The purities of compounds 5a-5r were analyzed via ultra-performance liquid chromatography, and their structures were elucidated by NMR, and HRMS. Additionally, the molecular structure of 5d was further confirmed by X-ray structure analysis. In vitro, the inhibitory activities of 5a-5r were tested against HepG2 cell lines by the CCK8 procedures. The IC₅₀ values of 0.17 - 69.89 μmol/L indicated the potential antitumor effectiveness of target compounds 5a-5r. Furthermore, compound 5c was selected to induce HepG2 cells apoptosis and conduct docking study, which considered as a new targeted antitumor agent.

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查尔酮介导和意外重排制备h -吡唑-呋喃[2,3-d]嘧啶衍生物作为有效的抗肿瘤药物

n -杂环的多功能性因其显著的生物活性而备受关注。本研究探索了一种新的查尔酮介导的意外重排反应，用于制备1h -吡唑-呋喃[2,3-d]嘧啶5a-5r。用超高效液相色谱法分析了化合物5a-5r的纯度，并用核磁共振和质谱法对其结构进行了鉴定。另外，通过x射线结构分析进一步证实了5d的分子结构。体外，采用CCK8程序检测5a-5r对HepG2细胞株的抑制活性。IC50值为0.17 ~ 69.89 μmol/L，表明目标化合物5a ~ 5r具有潜在的抗肿瘤作用。进一步选择化合物5c诱导HepG2细胞凋亡并进行对接研究，被认为是一种新的靶向抗肿瘤药物。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.