Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2022-10-13 , DOI: 10.1016/j.arabjc.2022.104351 Fangyao Su , Zhengyu Su , Qianrui Zhao , Zhe Zhao , Zhiyong Wu , Mingqin Zhao , Miao Lai
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Synthesis, thermal properties, as well as antifungal assessment of pyrazine esters were handed in this work. The metal-free esterification of pyrazinyl methanol and acid chloride derivatives in a stoichiometric ratio yielded the following compounds: pyrazin-2-ylmethyl benzoate (3a), (5-methylpyrazin-2-yl) methyl benzoate (3b), 1-(pyrazin-2-yl) ethyl benzoate (3c), 2-(pyrazin-2-yl) ethyl benzoate (3d), pyrazin-2-ylmethyl pivalate (3e). The spectral results totally showed that the synthesis conditions used permitted the compounds to be produced with great yield. The characterization included 1H NMR, 13C NMR, IR, HRMS and organoleptic tests. Their thermal degradation process was examined by using the TG (thermogravimetry) and DSC (differential scanning calorimeter) methods. The pyrolysis products of the pyrazine esters in inert and oxidative atmospheres were analyzed by the Py-GC/MS (pyrolysis–gas chromatography/mass spectrometry) method. It revealed that 3a–3e were totally evaporated throughout the pyrolysis experiments at low temperatures. And they evaporated with high relative contents in pure nitrogen (86.12%–94.17%) and oxidative (75.01%–88.85%) atmospheres, with only a small amount decomposing into a series of substances. Additionally, the in vitro antifungal effects of compounds 3a–3e against R. solani, P. nicotianae, F. oxysporum, F. graminearum, and F. moniliforme were further investigated using the mycelial growth rate methodology. The findings shown that compound 3c has 94% and 80% inhibitor rates at 0.5 mg/ml against R. solani and P. nicotianae, respectively, with an EC50 value (half maximum effective concentration) of 0.0191 mg/ml and 0.1870 mg/ml, respectively. Similarly, that of compounds 3a and 3b exhibited 82% and 91% at 0.5 mg/ml against R. solani, with an EC50 value of 0.0209 mg/ml and 0.0218 mg/ml, respectively. The molecular docking of compound 3c with SDH (Succinate dehydrogenase) was preliminarily performed to reveal the binding modes in active pocket and analyze the interactions between the molecules and the protein.
中文翻译:
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吡嗪酯的合成、热性能及抗真菌评价
这项工作对吡嗪酯的合成、热性能以及抗真菌性进行了评估。吡嗪甲醇和酰氯衍生物按化学计量比进行无金属酯化反应,得到以下化合物:吡嗪-2-基苯甲酸甲酯 ( 3a )、(5-甲基吡嗪-2-基) 苯甲酸甲酯 ( 3b )、1-(吡嗪) -2-基)苯甲酸乙酯( 3c )、2-(吡嗪-2-基)苯甲酸乙酯( 3d )、吡嗪-2-基甲基新戊酸酯( 3e )。光谱结果完全表明,所使用的合成条件允许化合物以高收率生产。表征包括1 H NMR、13C NMR、IR、HRMS 和感官测试。通过使用TG(热重)和DSC(差示扫描量热仪)方法检查它们的热降解过程。吡嗪酯在惰性和氧化气氛中的热解产物通过 Py-GC/MS(热解-气相色谱/质谱)方法进行分析。结果表明,在低温下的整个热解实验中, 3a-3e完全蒸发了。并且它们在纯氮(86.12%~94.17%)和氧化(75.01%~88.85%)气氛中相对含量较高,仅少量分解成一系列物质。此外,化合物3a-3e的体外抗真菌作用使用菌丝体生长速率方法进一步研究了立枯枯萎病菌、烟草假单胞菌、尖孢镰刀菌、禾谷镰刀菌和串珠镰刀菌。研究结果表明,化合物3c在 0.5 mg/ml 时对立枯病菌和烟草假单胞菌的抑制率分别为 94% 和 80% ,EC 50值(半最大有效浓度)为 0.0191 mg/ml 和 0.1870 mg/毫升,分别。类似地,化合物3a和3b在 0.5 mg/ml 时对立枯病菌的抑制率分别为82% 和 91%,EC 50值分别为 0.0209 mg/ml 和 0.0218 mg/ml。化合物3c的分子对接初步使用SDH(琥珀酸脱氢酶)揭示活性口袋中的结合模式并分析分子与蛋白质之间的相互作用。