Application of the Morita-Baylis-Hillman reaction in the synthesis of 3-[(N-cycloalkylbenzamido)methyl]-2-quinolones as potential HIV-1 integrase inhibitors

被引：50

作者：

Sekgota, Khethobole C. ^{[1
]}

Majumder, Swarup ^{[1
]}

Isaacs, Michelle ^{[3
]}

Mnkandhla, Dumisani ^{[3
]}

Hoppe, Heinrich C. ^{[2
,3
]}

Khanye, Setshaba D. ^{[1
,3
]}

Kriel, Frederik H. ^{[4
]}

Coates, Judy ^{[4
]}

Kaye, Perry T. ^{[1
,3
]}

机构：

[1] Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa

[2] Rhodes Univ, Dept Biochem & Microbiol, ZA-6140 Grahamstown, South Africa

[3] Rhodes Univ, Ctr Chem & Biomed Res, ZA-6140 Grahamstown, South Africa

[4] Mintek, Adv Mat Div, Ctr Met Based Drug Discovery, ZA-2125 Randburg, South Africa

来源：

BIOORGANIC CHEMISTRY | 2017年 / 75卷

基金：

英国医学研究理事会;

关键词：

2-quinolones; Synthesis; Morita_Baylis-Hillman; Bioassay; HIV-1 integrase inhibitors; REVERSE-TRANSCRIPTASE; QUINOLINE DERIVATIVES; DRUG-RESISTANCE; EFFICIENT ROUTE; ACID;

D O I：

10.1016/j.bioorg.2017.09.015

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：

A practicable six-step synthetic pathway has been developed to access a library of novel 3-[(N-cycloalk ylbenzamido) methyl]-2-quinolones using Morita-Baylis-Hillman methodology. These compounds and their 3-[(N-cycloalkylamino) methyl]-2-quinolone precursors have been screened as potential HIV-1 integrase (IN) inhibitors. A concomitant survey of their activity against HIV-1 protease and reverse-transcriptase reveals selective inhibition of HIV-1 IN. (C) 2017 Elsevier Inc. All rights reserved.

引用

页码：310 / 316

页数：7

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