根据曼尼奇反应合成和评价新黄酮类化合物抗氧化能力

Nguyễn Văn Sơn, VÕ THÀNH CÔNG, Phạm Văn Hùng
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引用次数: 0

摘要

以槲皮素为原料,用乙酸酐合成了4-(3,7-二乙酰氧基-5-羟基-4-氧基-4-铬-2-基)-1,2-苯二乙酸酯(1)。以1与多种胺和甲醛的曼尼希反应为基础,合成了6个新的衍生物2-7,在80℃下反应1-3 h,产率约为65- 86%。氨基甲基化优先发生在1的a环的C-6位置。采用FT-IR、1H-NMR、13C-NMR、ms等现代理化分析方法对合成的化合物进行了分子结构表征,并采用标准ABTS法对合成的化合物进行了抗氧化能力评价,结果表明,所有化合物均具有抗氧化能力,其中最佳化合物为3 (IC50 64.02±0.15µM)、5 (IC50 164.74±0.14µM)和7 (IC50 167.40±0.11µM),比Trolox标准(IC50 221.31±0.17µM)高1.4 ~ 3.4倍。这些都是抗氧化应用的潜在化合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
TỔNG HỢP VÀ ĐÁNH GIÁ KHẢ NĂNG KHÁNG OXY HÓA CỦA DẪN XUẤT FLAVONOIDS MỚI TRÊN CƠ SỞ PHẢN ỨNG MANNICH
We successfully synthesized  4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate (1) from Quercetin with acetic anhydride. Based on the Mannich reaction of 1 with various amines and formaldehyde, six novel derivatives 2-7 were synthesized and formed at 80℃ for 1-3 hours with yields of about 65- 86%. The aminomethylation occurred preferentially in the position at C-6 of the A-ring of 1. All synthesized compounds were determined by molecular structure by modern physicochemical analysis methods such as FT-IR, 1H-NMR, 13C-NMR, and MS. Moreover, the synthesized compounds were evaluated for their antioxidant capacity by the standard ABTS method, showing that all compounds have the antioxidant capacity, of which the best compounds were 3 (IC50 64.02±0.15 µM), 5 (IC50 164.74±0.14 µM) and 7 (IC50 167.40±0.11 µM) 1.4-3.4 times higher than Trolox standard (IC50 221.31±0.17 µM). These are potential compounds for antioxidant applications.
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