Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

被引：28

作者：

D'hooghe, Matthias ^{[1
]}

Vandekerckhove, Stephanie ^{[1
]}

Mollet, Karen ^{[1
]}

Vervisch, Karel ^{[1
]}

Dekeukeleire, Stijn ^{[1
]}

Lehoucq, Liesbeth ^{[1
]}

Lategan, Carmen ^{[2
]}

Smith, Peter J. ^{[2
]}

Chibale, Kelly ^{[3
,4
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, B-9000 Ghent, Belgium

[2] Univ Cape Town, Groote Schuur Hosp, OMB, Sch Med, ZA-7925 Observatory, South Africa

[3] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa

[4] Univ Cape Town, Inst Infect Dis & Mol Med, ZA-7701 Rondebosch, South Africa

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷

基金：

比利时弗兰德研究基金会;

关键词：

aminopropanes; antimalarial activity; aziridines; beta-lactams; ring opening; BETA-LACTAM ANTIBIOTICS; ERYTHROCYTE G-PROTEIN; ASYMMETRIC-SYNTHESIS; BUILDING-BLOCKS; REACTIVITY; TRANSFORMATION; DERIVATIVES; AZIRIDINES; CHEMISTRY; EPOXIDES;

D O I：

10.3762/bjoc.7.205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 2-amino-3-arylpropan-1-ols, anti-2-amino-3-aryl-3-methoxypropan-1-ols and anti-2-amino-1-arylpropan-1,3-diols were prepared selectively through elaboration of trans-4-aryl-3-chloro-beta-lactams. In addition, a number of 2-(azidomethyl)aziridines was converted into novel 2-[(1,2,3-triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC50-values of <= 25 mu M.

引用

页码：1745 / 1752

页数：8

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