A facile access to 2-substituted naphtho[2,3-g]quinoline-3-carboxylic acid esters via intramolecular cyclization and PyBOP-promoted functionalization

被引：5

作者：

Litvinova, Valeria A. ^{[1
]}

Tikhomirov, Alexander S. ^{[1
,2
]}

Ivanov, Ivan, V ^{[1
]}

Solovieva, Svetlana E. ^{[1
]}

Shchekotikhin, Andrey E. ^{[1
]}

机构：

[1] Gause Inst New Antibiot, 11 B Pirogovskaya St, Moscow 119021, Russia

[2] Mendeleyev Univ Chem Technol, 9 Miusskaya Sq, Moscow 125047, Russia

来源：

TETRAHEDRON | 2020年 / 76卷 / 36期

基金：

俄罗斯基础研究基金会;

关键词：

Anthraquinone; Quinoline; Heterocyclization; Functionalization; PyBOP; Aromatic nucleophilic substitution; BREAST-CANCER; QUINOLINES; DERIVATIVES; ACTIVATION; INHIBITORS; DISCOVERY; ANTITUMOR; DRUG; IDENTIFICATION; TRANSFORMATION;

D O I：

10.1016/j.tet.2020.131418

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heteroarene-fused derivatives of anthraquinone (anthracene-9,10-dione) represent an exceptionally productive class for the search for new anticancer compounds with improved properties. In this study, we report a convenient heterocyclization, which in three steps leads to 2-alkyl-, aryl-, or hydroxyl derivatives of 5,12-dimethoxynaphtho[2,3-g]quinoline-3-carboxylic acid esters. The scheme includes an alkylation of CH-acids with 2-(bromomethyl)-1,4-dimethoxy-3-nitroanthraquinone (8) followed by reductive cyclization and oxidative aromatization. To increase the series of naphtho[2,3-g]quinoline derivatives, a mild and effective PyBOP-mediated functionalization was developed, which introduced N-, S-, and O-nucleophiles at the 2-position of the quinoline core. We believe that this study allows to access a broad family of 2-substituted naphtho[2,3-g]quinolines and can be adapted for other quinoline derivatives or polyaromatic analogs. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：10