Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product.
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-diphenyl-2-picryl-hydrazyl free radical (DPPH(*)), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid (ABTS(*+)), N,N-dimethyl-p-phenylenediamine dihydrochloride radical cation (DMPD(*+)), and superoxide anion radical (O(2)(*-)) scavenging, reducing ability determination by the Fe(3+)-Fe(2+) and Cu(2+)-Cu(+) cupric reducing antioxidant capacity (CUPRAC) transformation methods, hydrogen peroxide scavenging, and ferrous ion (Fe(2+)) chelating activities. Moreover, these activities were compared to those of synthetic standard antioxidant compounds such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol, and trolox. The results showed that the synthesised bromophenols had effective antioxidant power.
Balaydin
Halis Türker
HT
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey.
Gülçin
Ílhami
Í
Menzek
Abdullah
A
Göksu
Süleyman
S
Şahin
Ertan
E
D000465:Algorithms; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry*; D001559:Benzhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D001577:Benzophenones / Q000138:chemical synthesis / Q000737:chemistry; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D011075:Polybrominated Biphenyls / Q000138:chemical synthesis* / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
C554615:5,5'-methylene bis(3,4-dibromobenzene-1,2-diol); D000975:Antioxidants; D001559:Benzhydryl Compounds; D001577:Benzophenones; D002396:Catechols; D016166:Free Radical Scavengers; D006842:Hydrocarbons, Brominated; D011075:Polybrominated Biphenyls; C010129:diphenylmethane