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二硫代氨基甲酰基黄酮类化合物抗氧化性能的构效关系研究

A Structure-Activity Relationship Study on the Antioxidant Properties of Dithiocarbamic Flavanones.

作者信息

Birsa Mihail Lucian, Sarbu Laura Gabriela

机构信息

Department of Chemistry, Alexandru Ioan Cuza University of Iasi, No. 11 Carol I Boulevard, 700506 Iasi, Romania.

出版信息

Antioxidants (Basel). 2024 Aug 8;13(8):963. doi: 10.3390/antiox13080963.

DOI:10.3390/antiox13080963
PMID:39199209
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11351990/
Abstract

The antioxidant properties of 3-dithiocarbamic flavanones have been investigated. The influence of the halogen substituents on ring A of the flavanones and the nature of the secondary amine from the dithiocarbamic moiety have been accounted. The results indicated that the presence of a halogen substituent at the C-8 position of the benzopyran ring induce better antioxidant properties against DPPH and ABTS than butylated hydroxytoluene (BHT) and ascorbic acid. The presence of a halogen substituent at the mentioned position appears to induce a higher stability for a free radical intermediate at the C-3 position of the benzopyran ring. A free radical enolate is most likely to be involved in the antioxidant activity of this dithiocarbamic flavanone. It is a stable intermediate that supports the influence of dithiocarbamic moiety on the antioxidant properties of the reported flavanones.

摘要

已对3-二硫代氨基甲酰基黄烷酮的抗氧化性能进行了研究。考虑了黄烷酮A环上卤素取代基的影响以及二硫代氨基甲酰基部分仲胺的性质。结果表明,苯并吡喃环C-8位存在卤素取代基时,其对DPPH和ABTS的抗氧化性能优于丁基化羟基甲苯(BHT)和抗坏血酸。上述位置存在卤素取代基似乎会使苯并吡喃环C-3位的自由基中间体具有更高的稳定性。自由基烯醇盐很可能参与了这种二硫代氨基甲酰基黄烷酮的抗氧化活性。它是一种稳定的中间体,支持二硫代氨基甲酰基部分对所报道黄烷酮抗氧化性能的影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/22a7e8bbce5b/antioxidants-13-00963-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/1ae25dfb0854/antioxidants-13-00963-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/7b623a089ad3/antioxidants-13-00963-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/22a7e8bbce5b/antioxidants-13-00963-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/1ae25dfb0854/antioxidants-13-00963-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/7b623a089ad3/antioxidants-13-00963-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f0da/11351990/22a7e8bbce5b/antioxidants-13-00963-sch003.jpg

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