期刊
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
卷 25, 期 5, 页码 685-695出版社
TAYLOR & FRANCIS LTD
DOI: 10.3109/14756360903514164
关键词
Antioxidant activity; bromination; bromophenols; natural product; radical scavenging
资金
- Ataturk University
- TUBITAK [107T348]
Bromination of bis(3,4-dimethoxyphenyl)methanone (5) gave four products (6-9) with mono, di, tri, and tetra Br under different conditions. Reduction and demethylation reactions of product 9 with tetra Br were performed, consecutively and a natural product, 5,5'-methylene bis(3,4-dibrombenzene-1,2-diol) (1), was obtained with a 53% yield. Five derivatives, (13-17) (bromophenols), of 1 were also synthesised. The antioxidant and radical scavenging activities of bromophenols 1 and 13-17 were determined by employing various in vitro assays such as 1,1-dipheny1-2-picryl-hydrazyl free radical (DPPH), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid (ABTS(center dot+)), N,N-dimethyl-p-phenylenediamine dihydrochloride radical cation (DMPD center dot+), and superoxide anion radical (O-2(center dot center dot)) scavenging, reducing ability determination by the Fe3+-Fe2+ and Cu2+-Cu+ cupric reducing antioxidant capacity (CUPRAC) transformation methods, hydrogen peroxide scavenging, and ferrous ion (Fe2+) chelating activities. Moreover, these activities were compared to those of synthetic standard antioxidant compounds such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), a-tocopherol, and trolox. The results showed that the synthesised bromophenols had effective antioxidant power.
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