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

Journal of Enzyme Inhibition and Medicinal Chemistry
Halis Türker BalaydinErtan Sahin

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-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 synthesise...Continue Reading

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Citations

Nov 22, 2011·Archives of Toxicology·İlhami Gülçin
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Ertan SahinAbdullah Menzek
Jun 3, 2011·International Journal of Food Sciences and Nutrition·Hülya Göçer, Ilhami Gülçin
Jul 12, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Betul ArabaciSaleh Alwasel
Dec 19, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Leyla Polat KoseClaudiu T Supuran
Jun 4, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Halis Türker BalaydınErtan Sahin
Mar 21, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Meryem TopalSaleh H Alwasel
Sep 22, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Yusuf AkbabaSükrü Beydemir
Aug 6, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Halis Türker BalaydinAbdullah Menzek
Sep 3, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Ilhami GülçinAkçahan Gepdiremen
Jan 15, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea ScozzafavaSaleh H Alwasel
Jul 3, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Parham TaslimiClaudiu T Supuran
Jul 7, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Fevzi TopalSaleh H Alwasel
Apr 22, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Hulya GocerClaudiu T Supuran
Dec 17, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Zübeyir Huyutİlhami Gülçin
Jun 19, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·M Hilal SehitogluHassan Y Aboul-Enein
Apr 4, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Meryem NarAbdullah Menzek
Apr 8, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Cebrail Gürsulİlhami Gülçin
Apr 30, 2015·Journal of the Science of Food and Agriculture·Songül ÇakmakçıPınar Kalın
Apr 15, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Burhanettin TuranClaudiu T Supuran
May 10, 2015·Bioorganic Chemistry·Necla Öztaşkınİlhami Gülçin
Jun 17, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Fazile Nur Ekinci AkdemirRecep Soslu
Aug 25, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Fazile Nur Ekinci AkdemirSaleh H Alwasel
Jun 9, 2017·Journal of Biochemical and Molecular Toxicology·Zeynep KöksalHasan Özdemir
Feb 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anna Kurek-GóreckaJerzy Stojko
Nov 16, 2019·Journal of Biochemical and Molecular Toxicology·Ramazan KalinHasan Ozdemir
Mar 18, 2020·Archives of Toxicology·İlhami Gulcin
Jul 20, 2021·Journal of Biomolecular Structure & Dynamics·Saman Zare GheshlaghiZeinab Faghih

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