Talaz Oktay, Gülçin Ilhami, Göksu Süleyman, Saracoglu Nurullah
Department of Chemistry, Faculty of Sciences, Atatürk University, 25240-Erzurum, Turkey.
Bioorg Med Chem. 2009 Sep 15;17(18):6583-9. doi: 10.1016/j.bmc.2009.07.077. Epub 2009 Aug 5.
An efficient synthesis of 5,10-dihydroindeno[1,2-b]indoles (3a-t) containing substituents such as methoxy, hydroxyl, and halogen (F, Cl, and Br) on indeno part was described. Antioxidant and radical scavenging activities of synthesized compounds (3a-t) were determined by various in vitro assays such as 1,1-diphenyl-2-picryl-hydrazyl free radicals (DPPH()), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid radicals (ABTS(+)), N,N-dimethyl-p-phenylenediamine dihydrochloride radicals (DMPD(+)), and superoxide anion radicals (O(2)(-)) scavenging, reducing ability determination by the Fe(3+)-Fe(2+) and Cu(2+)-Cu(+) (CUPRAC method) transformation methods, H(2)O(2) scavenging, and ferrous ion (Fe(2+)) chelating activities. Moreover, these activities were compared to synthetic and standard antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol, and trolox. The results showed that the synthesized compounds (3a-t) had effective antioxidant power.
描述了一种高效合成5,10 - 二氢茚并[1,2 - b]吲哚（3a - t）的方法，该化合物茚部分含有甲氧基、羟基和卤素（氟、氯和溴）等取代基。通过多种体外试验测定了合成化合物（3a - t）的抗氧化和自由基清除活性，如1,1 - 二苯基 - 2 - 苦基肼自由基（DPPH(·)）、2,2'- 偶氮 - 双（3 - 乙基苯并噻唑啉 - 6 - 磺酸）自由基（ABTS(·+)）、N,N - 二甲基 - 对苯二胺二盐酸盐自由基（DMPD(·+)）和超氧阴离子自由基（O₂(·-)）清除试验，通过Fe(³⁺) - Fe(²⁺)和Cu(²⁺) - Cu(⁺)（CUPRAC法）转化方法测定还原能力，H₂O₂清除试验以及亚铁离子（Fe(²⁺)）螯合活性。此外，将这些活性与合成抗氧化剂和标准抗氧化剂如丁基羟基茴香醚（BHA）、丁基羟基甲苯（BHT）、α - 生育酚和曲克芦丁进行了比较。结果表明，合成化合物（3a - t）具有有效的抗氧化能力。
