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酰胺腙衍生吡咯-2,5-二酮衍生物的合成及结构研究：潜在的抗炎剂。

Synthesis and Structural Study of Amidrazone Derived Pyrrole-2,5-Dione Derivatives: Potential Anti-Inflammatory Agents.

机构信息

Department of Organic Chemistry, Faculty of Pharmacy, Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toruń, Jurasza Str. 2, 85-089 Bydgoszcz, Poland.

Department of Analytical Chemistry and Applied Spectroscopy, Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina Str. 7, 87-100 Torun, Poland.

出版信息

Molecules. 2022 Apr 30;27(9):2891. doi: 10.3390/molecules27092891.

DOI:10.3390/molecules27092891
PMID:35566243
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9099820/
Abstract

1-pyrrole-2,5-dione derivatives are known for their wide range of pharmacological properties, including anti-inflammatory and antimicrobial activities. This study aimed to synthesize new 3,4-dimethyl--pyrrole-2,5-dione derivatives - in the reaction of -substituted amidrazones with 2,3-dimethylmaleic anhydride and evaluate their structural and biological properties. Compounds - were studied by the H-C NMR two-dimensional techniques (HMQC, HMBC) and single-crystal X-ray diffraction (derivatives and ). The anti-inflammatory activity of compounds - was examined by both an anti-proliferative study and a production study on the inhibition of pro-inflammatory cytokines (IL-6 and TNF-α) in anti-CD3 antibody- or lipopolysaccharide-stimulated human peripheral blood mononuclear cell (PBMC) cultures. The antibacterial activity of compounds against , , , , , , and strains was determined using the broth microdilution method. Structural studies of - revealed the presence of distinct and stereoisomers in the solid state and the solution. All compounds significantly inhibited the proliferation of PBMCs in anti-CD3-stimulated cultures. The strongest effect was observed for derivatives -. The strongest inhibition of pro-inflammatory cytokine production was observed for the most promising anti-inflammatory compound .

摘要

1-吡咯烷-2,5-二酮衍生物因其广泛的药理学特性而闻名，包括抗炎和抗菌活性。本研究旨在合成新的 3,4-二甲基--吡咯烷-2,5-二酮衍生物 - 在取代的 amidrazones 与 2,3-二甲基马来酸酐的反应中，并评估它们的结构和生物学性质。化合物 - 通过 H-C NMR 二维技术（HMQC、HMBC）和单晶 X 射线衍射（衍生物 和 ）进行研究。通过抗增殖研究和抑制抗 CD3 抗体或脂多糖刺激的人外周血单个核细胞（PBMC）培养物中促炎细胞因子（IL-6 和 TNF-α）的产生研究，检查了化合物 - 的抗炎活性。使用肉汤微量稀释法测定化合物 对 、 、 、 、 、 和 菌株的抗菌活性。 - 的结构研究表明，在固态和溶液中存在明显的 和 立体异构体。所有化合物均显著抑制抗 CD3 刺激培养物中 PBMC 的增殖。在研究的衍生物中，- 表现出最强的抑制作用。对于最有前途的抗炎化合物 ，观察到促炎细胞因子产生的最强抑制作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/b7445d156a70/molecules-27-02891-g010.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/bf6489dafab3/molecules-27-02891-sch001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/e0d9712d8340/molecules-27-02891-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/101b238757dd/molecules-27-02891-g005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/1817642fab9a/molecules-27-02891-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/4ee4e68a40d3/molecules-27-02891-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/b7445d156a70/molecules-27-02891-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/ef3788b00e80/molecules-27-02891-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/d55e35adcbef/molecules-27-02891-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/bf6489dafab3/molecules-27-02891-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/3a65ed239d03/molecules-27-02891-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/e0d9712d8340/molecules-27-02891-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/101b238757dd/molecules-27-02891-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/095d39175ae5/molecules-27-02891-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/314a9046abb8/molecules-27-02891-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/1817642fab9a/molecules-27-02891-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/4ee4e68a40d3/molecules-27-02891-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fcc8/9099820/b7445d156a70/molecules-27-02891-g010.jpg

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