One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study
One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study
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DOI：
10.1007/s00706-015-1517-5
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发表时间：
2015-12-01
影响因子：
1.8
通讯作者：
Apak, Resat
中科院分区：
文献类型：
--
作者：
Deniz, Nahide Gulsah;Ozyurek, Mustafa;Apak, Resat
本文报道了S，S和S，O-取代1，4-萘醌的一锅法合成、结构研究和抗氧化活性研究。研究了2，3-二氯-1，4-萘酚与含硫、含氧亲核试剂的多组分反应，得到了高官能化的S、S和S，O-取代的1，4-萘酚衍生物。所有新化合物均经H-1、F-19和C-13核磁共振波谱、质谱学和傅立叶变换红外光谱确证。用X射线衍射法测定了2，3-dihydro-2-(hydroxymethyl)naphtho[2，3-b]-1，4-oxathiin-5，10-dione的晶体结构。分别采用铜还原抗氧化剂容量法和DPPH法对合成化合物的抗氧化能力和清除自由基活性进行了筛选。3-Chloro-2-[3-(3-chloro-1，4-dihydro-1，4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1，4-naphthoquinone显示出最高的抗氧化能力，为0.63Cuprc，降低了抗氧化能力--Trolox当量抗氧化能力系数。
In the present study, we reported the one-pot synthesis of S,S- and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur- and oxygen-containing nucleophiles were investigated to obtain highly functionalized S,S- and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of H-1, F-19, and C-13 nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient.