Synthesis and evaluation of new amidrazone-derived hydrazides as a potential anti-inflammatory agents.

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-06-27 DOI:10.1007/s00706-018-2197-8

Renata Paprocka, Małgorzata Wiese-Szadkowska, Anna Helmin-Basa, Liliana Mazur, Jolanta Kutkowska, Jacek Michałkiewicz, Bożena Modzelewska-Banachiewicz, Leszek Pazderski

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Abstract

Abstract: The series of new hydrazide derivatives were synthesized in reactions of N³-substituted amidrazones with cyclic anhydrides as potential anti-inflammatory and antibacterial agents. The compounds were characterized by ¹H-¹³C two-dimensional NMR techniques, which revealed the presence of two tautomeric forms in DMSO-d₆ solutions, while the molecular structure of one species was confirmed by single-crystal X-ray diffraction. The anti-inflammatory effects of hydrazides on peripheral blood mononuclear cells were experimentally evaluated. Three compounds showed antiproliferative activity comparable to ibuprofen. One derivative demonstrated strong reduction of lymphocyte proliferation stimulated by anti-CD3 antibody (by 90%) and PHA, as well as low cell toxicity. The obtained compounds exhibited relatively weak antibacterial activity; they were more effective against Gram-positive bacterial strains.

Graphical abstract:

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合成和评估作为潜在抗炎剂的新型脒基肼。

摘要：在 N3 取代的脒酮与环酸酐的反应中合成了一系列新的酰肼衍生物，作为潜在的消炎药和抗菌药。通过 1H-13C 二维核磁共振技术对这些化合物进行了表征，发现在 DMSO-d6 溶液中存在两种同分异构形式，而单晶 X 射线衍射则证实了其中一种的分子结构。实验评估了酰肼对外周血单核细胞的抗炎作用。三种化合物显示出与布洛芬相当的抗增殖活性。其中一种衍生物在抗 CD3 抗体（90%）和 PHA 的刺激下能显著降低淋巴细胞的增殖，而且细胞毒性较低。获得的化合物表现出相对较弱的抗菌活性；它们对革兰氏阳性细菌菌株更有效：

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来源期刊

Monatshefte Fur Chemie 化学-化学综合

CiteScore

3.70

自引率

5.60%

发文量

116

审稿时长

3.3 months

期刊介绍： "Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.