Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

被引：23

作者：

Mayer, Szabolcs ^{[1
]}

Keglevich, Peter ^{[1
]}

Abranyi-Balogh, Peter ^{[2
]}

Szigetvari, Aron ^{[3
]}

Dekany, Miklos ^{[3
]}

Szantay, Csaba, Jr. ^{[3
]}

Hazai, Laszlo ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Fac Chem Technol & Biotechnol, Dept Organ Chem & Technol, Gellert Ter 4, H-1111 Budapest, Hungary

[2] Res Ctr Nat Sci, Inst Organ Chem, Med Chem Res Grp, Magyar Tudosok Krt 2, H-1117 Budapest, Hungary

[3] Gedeon Richter Plc, Spectroscop Res Dept, POB 27, H-1475 Budapest, Hungary

来源：

MOLECULES | 2020年 / 25卷 / 04期

关键词：

flavonoid; chrysin; aminoflavonoid; anticancer activity; Smiles rearrangement; CELL-LINES; INHIBITORS; AMINOFLAVONES; FEASIBILITY; FLAVONOIDS; DESIGN; SERIES;

D O I：

10.3390/molecules25040888

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Chrysin is a naturally occurring flavonoid with mild anticancer activity. In this paper we report the synthesis of new chrysin derivatives alkylated with N-phenylchloroacetamides in position 7. A novel method was developed for the preparation of 7-aminochrysin derivatives via the Smiles rearrangement, resulting in diphenylamine-type compounds. In silico studies of the Smiles rearrangement were performed. We also present the in vitro antiproliferative activity of the synthesized compounds against 60 human tumor cell lines (NCI60). The most potent derivative exhibited nanomolar antitumor activity on the MCF7 cell line of breast cancer (GI(50) = 30 nM) and on the HCT-15 cell line of colon cancer (GI(50) = 60 nM).

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页数：14

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