Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product


Balaydin H. T. , GÜLÇİN İ., MENZEK A., GÖKSU S., ŞAHİN E.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.25, no.5, pp.685-695, 2010 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 25 Issue: 5
  • Publication Date: 2010
  • Doi Number: 10.3109/14756360903514164
  • Title of Journal : JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Page Numbers: pp.685-695
  • Keywords: Antioxidant activity, bromination, bromophenols, natural product, radical scavenging, IN-VITRO ANTIOXIDANT, ANTIRADICAL ACTIVITIES, ANTIMICROBIAL ACTIVITIES, ALGA, INHIBITORS, REARRANGEMENT, EFFICIENT, CAPACITY, EXTRACT, PTP1B

Abstract

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.