Synthesis and antiproliferative activities of polymethoxyflavones aminoalkyl and amino acid derivatives

IF 1.3 3区化学 Q3 CHEMISTRY, ORGANIC

Heterocyclic Communications Pub Date : 2020-01-01 DOI:10.1515/hc-2020-0010

Liqiong Ran, Xue-li Li, Manhui Liu, Qiu-an Wang

引用次数: 1

Abstract

Abstract Twelve novel aminoalkyl derivatives 3a-3f, 4a-4f and four novel amino acid derivatives 5a, 5b, 6a and 6b of polymethoxyflavones 1 and 2 were synthesized through regioselective demethylation, etherification, amination, EDCl-mediated amide condensation and alkaline hydrolysis, using tangeretin and nobiletin as starting materials. Their antiproliferative activities against four different human cancer cell lines (Aspc-1, SUN5, HepG-2 and HCT116) were evaluated by in vitro CCK-8 assay. The results show that the majority of the synthetic compounds exhibited moderate to good antiproliferative activity. In particular, the antiproliferative activity of compound 5b against HepG-2 cells (IC50 0.057 μM) was equal to the positive control drug Staurosporine (IC50 0.0575 μM).

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聚甲氧基黄酮-氨基烷基及其衍生物的合成及其抗增殖活性

摘要以唐和诺比林为原料，通过区域选择性脱甲基、醚化、胺化、EDCl介导的酰胺缩合和碱性水解，合成了12个新的聚甲氧基黄酮1和2的氨基烷基衍生物3a-3f、4a-4f和4个新的氨基酸衍生物5a、5b、6a和6b。通过体外CCK-8试验评估了它们对四种不同的人癌症细胞系（Aspc-1、SUN5、HepG-2和HCT116）的抗增殖活性。结果表明，大多数合成化合物表现出中等至良好的抗增殖活性。特别地，化合物5b对HepG-2细胞的抗增殖活性（IC50 0.057μM）等于阳性对照药物Staurosporine（IC50 0.05 75μM）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Heterocyclic Communications 化学-有机化学

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

1.4 months

期刊介绍： Heterocyclic Communications (HC) is a bimonthly, peer-reviewed journal publishing preliminary communications, research articles, and reviews on significant developments in all phases of heterocyclic chemistry, including general synthesis, natural products, computational analysis, considerable biological activity and inorganic ring systems. Clear presentation of experimental and computational data is strongly emphasized. Heterocyclic chemistry is a rapidly growing field. By some estimates original research papers in heterocyclic chemistry have increased to more than 60% of the current organic chemistry literature published. This explosive growth is even greater when considering heterocyclic research published in materials science, physical, biophysical, analytical, bioorganic, pharmaceutical, medicinal and natural products journals. There is a need, therefore, for a journal dedicated explicitly to heterocyclic chemistry and the properties of heterocyclic compounds.