Synthesis of 2,3-dihydroxy-3-( N -substituted carbamoyl)propylphosphonic acid derivatives as hybrid DOXP-fosmidomycin analogues

被引：3

作者：

Mutorwa, Marius K. ^{[1
,5
]}

Lobb, Kevin A. ^{[1
,2
]}

Klein, Rosalyn ^{[1
,2
]}

Blatch, Gregory L. ^{[2
,3
,4
]}

Kaye, Perry T. ^{[1
,2
]}

机构：

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

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

[3] Rhodes Univ, Biomed Biotechnol Res Unit, ZA-6140 Makhanda Grahamstown, South Africa

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

[5] Namibia Univ Sci & Technol, Nat & Appl Sci, Windhoek, Namibia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2022年 / 1256卷

基金：

英国医学研究理事会;

关键词：

DOXP-fosmidomycin hybrid analogues; Synthesis; STD-NMR; In silico docking; 1-DEOXY-D-XYLULOSE-5-PHOSPHATE REDUCTOISOMERASE; ALPHA; BETA-UNSATURATED AMIDES; ISOPRENOID BIOSYNTHESIS; ANTIMALARIAL ACTIVITY; ESTER PRODRUGS; PHOSPHATE; INHIBITORS; FR900098; PATHWAY; ARYL;

D O I：

10.1016/j.molstruc.2022.132453

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A B S T R A C T A six-step synthetic pathway has been established to access a series of racemic 2,3-dihydroxy-3-(N- substituted carbamoyl)propylphosphonic acid derivatives, designed to contain structural features common to both the natural substrate 1-deoxy-D-xylulose 5-phosphate (DOXP) of the Plasmodium falciparum (Pf) DXR enzyme and its known inhibitor, fosmidomycin. Positive STD-NMR and in silico docking data obtained for some of the compounds indicate their capacity to bind to the analogous E.coli DXR enzyme.(c) 2022 Elsevier B.V. All rights reserved.

引用

页数：6

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