Transition-metal-free, atom-economical cascade synthesis of novel 2-sulfonated-benzo[f][1,7]naphthyridines and their cytotoxic activities

被引：8

作者：

Arepalli, Sateesh Kumar ^{[1
]}

Choi, Yunseon ^{[1
]}

Lee, Kiho ^{[2
]}

Kang, Jong-Soon ^{[3
]}

Jung, Jae-Kyung ^{[1
]}

Lee, Heesoon ^{[1
]}

机构：

[1] Chungbuk Natl Univ, Coll Pharm, Chungbuk 28160, South Korea

[2] Korea Univ, Coll Pharm, Sejong 30019, South Korea

[3] Korea Res Inst Biosci & Biotechnol, Chungbuk 28116, South Korea

来源：

TETRAHEDRON | 2018年 / 74卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

Sulfonated benzo[f][1,7]naphthyridines; Transition-metal-free; One-pot C-S & C-C bonds formation; Atom-economy; Cytotoxic agents; NF-KAPPA-B; CATALYZED ALLYLIC SULFONYLATION; HETEROCYCLIC KETENE AMINALS; TOPOISOMERASE-I INHIBITORS; TERT-BUTYL HYDROPEROXIDE; ONE-POT; BIOLOGICAL EVALUATION; COMPREHENSIVE SURVEY; ANTICANCER AGENTS; ARYL SULFONES;

D O I：

10.1016/j.tet.2018.02.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, transition-metal-free cascade synthetic method has been developed for new 2-aryl/heteroaryl sulfonated benzon[f],[1,7]naphthyridines. It is tert-butyl hydroperoxide (TBHP) mediated highly regioselective sulfonylation cyclization aromatization process between N-(3-arylTheteroarylprop-2-yn-1-yl)quinolin-3-amines and aryl/heteroaryl sulfonylhydrazides. This synthetic protocol offers one-step strategy for C S and C C bond formations with a broad range of functional group tolerance. It is a simple, mild, and atom-economical route for the synthesis of various valuable functionalized 1, 2-aryl/heteroaryl sulfonated benzo[f][1,7]naphthyridines in moderate yields. Since the core motif of 2-sulfonated benzo[f][1,7]naphthyridines are biologically and pharmaceutically important (TLR activity 7, 8 modulators). Additionally, the synthesized derivatives were evaluated for their in vitro cytotoxic activities against six human cancer cell lines including lung (NCIH23), colon (HCT15), gastric (NUCG-3), renal (ACHN), prostate (PC-3), and breast (MDA-MB-231) cell lines. These compounds displayed significant cytotoxic activities against all tested human cancer cell lines. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1646 / 1654

页数：9

共 1 条

[1] A facile one-pot regioselective synthesis of functionalized novel benzo[f] chromeno[4,3-b][1,7]naphthyridines and benzo[f][1,7]naphthyridines via an imino Diels-Alder reaction
Arepalli, Sateesh Kumar
Park, Byeongwoo
Jung, Jae-Kyung
Lee, Kiho
Lee, Heesoon
TETRAHEDRON LETTERS, 2017, 58 (05) : 449 - 454

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