Design, Synthesis and Biological Evaluation of 4-Hydroxy-2-Thioxo-4-Trifluoromethyl-Hexahydro-Pyrimidin-5-yl]-p-Tolyl-Methanone Derivatives as Potent Anti-Inflammatory and Antimicrobial Agents

IF 2.4 3区 化学 Q2 CHEMISTRY, ORGANIC
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Abstract

A series of new 4-hydroxy-2-thioxo-4-trifluoromethyl-hexahydro-pyrimidin-5-yl]-p-tolyl-methanone derivatives were synthesized through one-pot three-component method using 4,4,4-trifluoro-1-p-tolyl-butane-1,3-dione, thiourea, and various substituted benzaldehydes. The structures of newly synthesized products were elucidated by spectroscopic studies such as IR, NMR (proton and carbon), mass spectra, and elemental analyses. The final products were screened for their antioxidant activity, anti-inflammatory activity against LPS-induced cell death in RAW 264.7 macrophage cell lines, antibacterial and antifungal activity using in vitro methods. The results revealed that the compounds such as 10e and 10i against DPPH and H2O2; 10a, 10e, 10h, and 10i against LPS induced inflammation in RAW 264.7 cell lines; 10a, 10b, 10c, 10d, and 10e against all the microbial strains tested have exhibited higher content of activity in vitro than the rest of the title compounds when compared to the standard drugs. In overall, 10a, and 10e have shown the most promising activity against all the systems tested. Hence, among all the title compounds, at least a few will stand as next generation antioxidant, anti-inflammatory and antimicrobial agents in future.
4-Hydroxy-2-Thioxo-4-Trifluoromethyl-Hexahydro-Pyrimidin-5-yl]-p-Tolyl-Methanone Derivatives as Potent Anti-Inflammatory and Anticroicroial Agents 的设计、合成和生物学评价
使用 4,4,4-三氟-1-对甲苯基丁烷-1,3-二酮、硫脲和各种取代的苯甲醛,通过一锅三组分法合成了一系列新的 4-羟基-2-硫酮-4-三氟甲基-六氢嘧啶-5-基]-对甲苯基甲酮衍生物。通过红外光谱、核磁共振(质子和碳)、质谱和元素分析等光谱研究,阐明了新合成产物的结构。采用体外方法筛选了最终产物的抗氧化活性、抗 LPS 诱导的 RAW 264.7 巨噬细胞系细胞死亡的抗炎活性、抗菌和抗真菌活性。结果表明,与标准药物相比,10e 和 10i 等化合物对 DPPH 和 H2O2 的抗性;10a、10e、10h 和 10i 对 RAW 264.7 细胞系中 LPS 诱导的炎症的抗性;10a、10b、10c、10d 和 10e 对所有受试微生物菌株的抗性,在体外表现出比其他标题化合物更高的活性含量。总的来说,10a 和 10e 对所有受试系统都表现出了最有希望的活性。因此,在所有标题化合物中,至少有几种将来会成为下一代抗氧化、抗炎和抗菌剂。
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来源期刊
Polycyclic Aromatic Compounds
Polycyclic Aromatic Compounds 化学-有机化学
CiteScore
3.70
自引率
20.80%
发文量
412
审稿时长
3 months
期刊介绍: The purpose of Polycyclic Aromatic Compounds is to provide an international and interdisciplinary forum for all aspects of research related to polycyclic aromatic compounds (PAC). Topics range from fundamental research in chemistry (including synthetic and theoretical chemistry) and physics (including astrophysics), as well as thermodynamics, spectroscopy, analytical methods, and biology to applied studies in environmental science, biochemistry, toxicology, and industry. Polycyclic Aromatic Compounds has an outstanding Editorial Board and offers a rapid and efficient peer review process, as well as a flexible open access policy.
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