Synthesis of N-Substituted phosphoramidic acid esters as "reverse" fosmidomycin analogues

被引：9

作者：

Adeyemi, Christiana M. ^{[1
]}

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

Isaacs, Michelle ^{[3
]}

Klein, Rosalyn ^{[1
,3
]}

Lobb, Kevin A. ^{[1
,3
]}

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

来源：

TETRAHEDRON | 2019年 / 75卷 / 16期

基金：

英国医学研究理事会;

关键词：

Reverse fosmidomycin analogues; N-benzylated phosphoramidates; Synthesis; Bioassay; HYDROAMINATION; ANTIMALARIAL; PRODRUGS;

D O I：

10.1016/j.tet.2019.02.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic pathway to a series of novel "reverse" fosmidomycin analogues has been developed, commencing from substituted benzylamines. In these analogues, the fosmidomycin hydroxamate moiety is reversed and the tetrahedral methylene carbon adjacent to the phosphonate moiety is replaced by a nitrogen atom bearing different benzyl groups. The resulting phosphonate esters were designed as potential antimalarial "pro-drugs". (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：2371 / 2378

页数：8

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