Improved synthesis and anti-inflammatory activity of new fluorinated dihydropyranonaphthoquinone compounds

IF 2.2 4区医学 Q3 CHEMISTRY, MEDICINAL

Bioorganic & Medicinal Chemistry Letters Pub Date : 2025-10-11 DOI:10.1016/j.bmcl.2025.130434

Quynh Giang Nguyen Thi , Ha Thanh Nguyen , Tuyet Anh Dang Thi , Kieu Trinh Nguyen Thi , Giang Le-Nhat-Thuy , Phuong Hoang Thi , Tuan Anh Nguyen , Mai Dang Thi , Ha Nguyen Thi Thu , Hoang Sa Nguyen , Tuyen Van Nguyen

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Abstract

This study presents the synthesis of new fluorinated dihydropyranonapthoquinone compounds by means of microwave-prompted four-component reactions using lawson, fluorinated aromatic aldehydes, ethyl 4,4,4-trifluoroacetoacetate and ammonium acetate. The products were thoroughly characterized by spectroscopic methods and assessed for their anti-inflammatory activity in lipopolysaccharide-stimulated RAW264.7 macrophage cells. All synthesized compounds demonstrated notable inhibitory effects on NO production with IC₅₀ ranging from 1.67 ± 0.02 to 28.81 ± 2.44 μM without causing significant toxicity. Interestingly, compound 8n showed the most potent NO inhibitory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with IC₅₀ value of 1.67 ± 0.02 μM. Moreover, compounds 8c,h,i,l significantly decreased the levels of pro-inflammatory cytokines IL-1β and IL-6 in LPS-stimulated RAW264.7 macrophages. These results indicate the potential of these compounds as promising candidates for the development of new anti-inflammatory agents.

Abstract Image

查看原文本刊更多论文

新型氟化二氢吡喃萘醌化合物的改进合成及其抗炎活性。

采用微波四组份反应，以lawson、氟化芳醛、4,4,4-三氟乙酸乙酯和乙酸铵为原料，合成了新的氟化二氢吡萘醌类化合物。通过光谱方法对产物进行了全面表征，并对脂多糖刺激的RAW264.7巨噬细胞进行了抗炎活性评估。所有化合物均具有显著的抑制NO生成作用，IC50值在1.67 ± 0.02 ~ 28.81 ± 2.44 μM之间，无明显毒性。有趣的是，化合物8n对脂多糖（LPS）刺激的RAW264.7巨噬细胞的NO抑制活性最强，IC50值为1.67 ± 0.02 μM。此外，化合物8c、h、i、l显著降低lps刺激RAW264.7巨噬细胞中促炎因子IL-1β和IL-6的水平。这些结果表明这些化合物具有开发新型抗炎药的潜力。

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来源期刊

Bioorganic & Medicinal Chemistry Letters 医学-医药化学

CiteScore

5.70

自引率

3.70%

发文量

463

审稿时长

27 days

期刊介绍： Bioorganic & Medicinal Chemistry Letters presents preliminary experimental or theoretical research results of outstanding significance and timeliness on all aspects of science at the interface of chemistry and biology and on major advances in drug design and development. The journal publishes articles in the form of communications reporting experimental or theoretical results of special interest, and strives to provide maximum dissemination to a large, international audience.