Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity

被引：19

作者：

Aksenov, Nicolai A. ^{[1
]}

Aksenov, Alexander, V ^{[1
]}

Kirilov, Nikita K. ^{[1
]}

Arutiunov, Nikolai A. ^{[1
]}

Aksenov, Dmitrii A. ^{[1
]}

Maslivetc, Vladimir ^{[2
]}

Zhao, Zhenze ^{[2
]}

Du, Liqin ^{[2
]}

Rubin, Michael ^{[1
,3
]}

Kornienko, Alexander ^{[2
]}

机构：

[1] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355009, Russia

[2] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA

[3] Univ Kansas, Dept Chem, 1567 Irving Hill Rd, Lawrence, KS 66045 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 34期

基金：

美国国家卫生研究院; 俄罗斯基础研究基金会;

关键词：

EFFICIENT SYNTHESIS; MEDIATED SYNTHESIS; POTENT INHIBITORS; 1,2,4-TRIAZOLES; DERIVATIVES; CYCLIZATION; ANALOGS; ACID;

D O I：

10.1039/d0ob01007c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4 ',3 '-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes in PPA. Several of the synthesized triazoles showed promising anticancer activity by inducing differentiation in neuroblastoma cancer cells. Due to the urgent need for novel differentiation agents for neuroblastoma therapy, this finding warrants further evaluation of this class of compounds against neuroblastoma.

引用

页码：6651 / 6664

页数：14

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