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源自1-羟基-2-乙酰萘酮的席夫碱的合成、表征、光谱研究及生物学评价

Synthesis, characterization, spectroscopic studies and biological evaluation of Schiff bases derived from 1-hydroxy-2-acetonapthanone.

作者信息

Vhanale B T, Deshmukh N J, Shinde A T

机构信息

Department of Chemical Sciences, N.E.S. Science College, Nanded, Maharashtra, 431605, India.

出版信息

Heliyon. 2019 Nov 14;5(11):e02774. doi: 10.1016/j.heliyon.2019.e02774. eCollection 2019 Nov.

Abstract

The four Schiff bases were synthesized by the condensation reaction of 1(1-hydroxynaphthalen-2-yl)ethanone, 1-(4-chloro-1hydroxynaphthalen-2-yl)ethanone and 1-(4-bromo-1-hydroxynaphthalen-2-yl)ethanone with propane-1,3-diamine and pentane-1,3-diamine. The structural analysis is done by UVvis., FT-IR, H NMR, C NMR, LCMS and elemental analyses. These compounds were assayed for antibacterial ( and activity and antioxidant ( and ) activity. The antibacterial and antioxidant activities of synthesized Schiff bases exhibited better degrees of inhibitory effects. Among these, Schiff base 2,2'-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-chloronaphthalen-1-ol) exhibited excellent antibacterial activity with MICs of 0.12, 0.25, 0.5 and 1 mg/ml against and . Furthermore, two Schiff bases such as, 2,2'-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(naphthalen-1-ol) and 2,2'-((pentane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-bromonaphthalen-1-ol) exhibited promising antioxidant activity.

摘要

通过1-(1-羟基萘-2-基)乙酮、1-(4-氯-1-羟基萘-2-基)乙酮和1-(4-溴-1-羟基萘-2-基)乙酮与1,3-丙二胺和1,3-戊二胺的缩合反应合成了四种席夫碱。通过紫外可见光谱、傅里叶变换红外光谱、氢核磁共振、碳核磁共振、液相色谱-质谱联用和元素分析进行结构分析。对这些化合物进行了抗菌(对 和 )活性和抗氧化(对 和 )活性测定。合成的席夫碱的抗菌和抗氧化活性表现出较好的抑制效果。其中,席夫碱2,2'-((丙烷-1,3-二亚基双(氮杂亚甲基))双(乙烷-1-亚基-1-亚基))双(4-氯萘-1-醇)对 和 表现出优异的抗菌活性,最低抑菌浓度分别为0.12、0.25、0.5和1mg/ml。此外,两种席夫碱,如2,2'-((丙烷-1,3-二亚基双(氮杂亚甲基))双(乙烷-1-亚基-1-亚基))双(萘-1-醇)和2,2'-((戊烷-1,3-二亚基双(氮杂亚甲基))双(乙烷-1-亚基-1-亚基))双(4-溴萘-1-醇)表现出有前景的抗氧化活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d652/6859237/a2aac74521d2/gr1.jpg

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