姜黄素模拟物的合成、表征、晶体结构和抗增殖性能

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-06-24 DOI:10.1080/00397911.2025.2520609

Aisha A. Alsfouk (Data curation Funding acquisition Methodology Validation Writing – original draft) , Benson M. Kariuki (Data curation Formal analysis Investigation Methodology Resources Software Validation Visualization Writing – original draft) , Asmaa Saleh (Data curation Funding acquisition Project administration Validation Visualization Writing – original draft) , Aladdin M. Srour (Conceptualization Investigation Methodology Supervision Validation Visualization Writing – original draft Writing – review & editing)

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引用次数: 0

摘要

以具有仲胺环的芳香醛（2a-c）为原料，采用碱催化缩合法（KOH/EtOH）合成了3个新的4-哌啶酮衍生物（3a-c），具体为哌啶、啉和甲基哌嗪。通过x射线晶体学对这三种新合成的衍生物进行了表征，并根据MTT试验程序评估了它们对三种不同的人类癌细胞系的抗增殖作用：乳腺癌（MCF-7）、肝癌（HepG-2）和结直肠癌（HCT-116），以及正常细胞系（RPE1）。其中，化合物3c对MCF-7和HepG-2的IC50分别为1.07±0.04 μM和2.55±0.07 μM，与标准参比品阿霉素的IC50分别为5.38±0.05 μM和4.25±0.01 μM相比，均表现出最高的抑制效果。此外，分子对接研究证实，化合物3c在人周期蛋白依赖性激酶2 （CDK2）的ATP结合位点内具有稳定的相互作用。本文介绍了三种有前景的中间体在药物化学领域的进一步研究。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Synthesis, characterization, crystal structure and anti-proliferative properties of curcumin mimic conjugates

Three novel 4-piperidone-based derivatives (3a–c) were synthesized utilizing the base-catalyzed condensation method (KOH/EtOH) with aromatic aldehydes (2a–c) featuring secondary amine rings, specifically piperidine, morpholine, and methyl piperazine. The three newly synthesized derivatives were characterized through X-ray crystallography, and their anti-proliferative effects were assessed against three different human cancer cell lines: breast carcinoma (MCF-7), liver cancer (HepG-2), and colorectal carcinoma (HCT-116), along with a normal cell line (RPE1), following the MTT assay procedure. Among them, compound 3c demonstrated the highest efficacy against all tested cell lines, demonstrating IC₅₀ = 1.07 ± 0.04 μM for MCF-7 and 2.55 ± 0.07 μM for HepG-2, compared to the standard reference, Doxorubicin, which had IC₅₀ = 5.38 ± 0.05 μM and 4.25 ± 0.01 μM, respectively. Moreover, a molecular docking study confirmed the stable interaction of compound 3c within the ATP binding site of human cyclin-dependent kinase 2 (CDK2). This study introduces three promising intermediates for further research in medicinal chemistry.

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.