884489-14-9Relevant academic research and scientific papers
Visible-Light-Promoted Decarboxylative Giese Reactions of α-Aryl Ethenylphosphonates and the Application in the Synthesis of Fosmidomycin Analogue
Guo, Ting,Zhang, Li,Fang, Yewen,Jin, Xiaoping,Li, Yan,Li, Ruifeng,Li, Xie,Cen, Wu,Liu, Xiaobo,Tian, Zongming
supporting information, p. 1352 - 1357 (2018/02/12)
An approach for the synthesis of α-aryl alkylphosphonates based on visible-light photocatalytic Giese reaction of α-aryl vinylphosphonates with aliphatic carboxylic acids has been successfully developed. This protocol tolerates a wide range of functional
Antimalarial and structural studies of pyridine-containing inhibitors of 1-deoxyxylulose-5-phosphate reductoisomerase
Xue, Jian,Diao, Jiasheng,Cai, Guobin,Deng, Lisheng,Zheng, Baisong,Yao, Yuan,Song, Yongcheng
supporting information, p. 278 - 282 (2013/03/29)
1-Deoxy-d-xylulose-5-phosphate reductoisomerase (DXR) in the nonmevalonate isoprene biosynthesis pathway is a target for developing antimalarial drugs. Fosmidomycin, a potent DXR inhibitor, showed safety as well as efficacy against Plasmodium falciparum malaria in clinical trials. On the basis of our previous quantitative structure-activity relationship (QSAR) and crystallographic studies, several novel pyridine-containing fosmidomycin derivatives were designed, synthesized, and found to be highly potent inhibitors of P. falciparum DXR (PfDXR) having Ki values of 1.9-13 nM, with the best one being ～11× more active than fosmidomycin. These compounds also potently block the proliferation of multidrug resistant P. falciparum with EC 50 values as low as 170 nM. A 2.3 A? crystal structure of PfDXR in complex with one of the inhibitors is reported, showing that the flexible loop of the protein undergoes conformational changes upon ligand binding and a hydrogen bond and favorable hydrophobic interactions between the pyridine group and the PfDXR account for the enhanced activity.
ORGANOPHOSPHORIC DERIVATIVES USEFUL AS ANTI-PARASITIC AGENTS
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Page/Page column 36, (2008/06/13)
The present invention relates to novel phosphonic acid compounds having the structural formula (I): wherein: (a) R is a group of 1 to 5 substituents independently selected from the group consisting of fluoro, chloro, bromo, C1-4 alkoxy, C1
Synthesis of α-aryl-substituted and conformationally restricted fosmidomycin analogues as promising antimalarials
Haemers, Timothy,Wiesner, Jochen,Busson, Roger,Jomaa, Hassan,Van Calenbergh, Serge
, p. 3856 - 3863 (2007/10/03)
Fosmidomycin represents a new antimalarial drug that acts by inhibition of 1-deoxy-D-xylulose 5-phosphate reductoisomerase, an essential enzyme of the mevalonate-independent pathway of isoprenoid biosynthesis. This work describes the synthesis of a series
Synthesis and antimalarial activity of chain substituted pivaloyloxymethyl ester analogues of Fosmidomycin and FR900098
Kurz, Thomas,Schlueter, Katrin,Kaula, Uwe,Bergmann, Baerbel,Walter, Rolf D.,Geffken, Detlef
, p. 5121 - 5135 (2007/10/03)
Fosmidomycin is a promising antimalarial drug candidate with a unique chemical structure and a novel mode of action. Chain substituted pivaloyloxymethyl ester derivatives of Fosmidomycin and its acetyl analogue FR900098 have been synthesized and their in vitro antimalarial activity versus the Chloroquine sensitive strain 3D7 of Plasmodium falciparum has been determined.
Synthesis of α-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors
Haemers, Timothy,Wiesner, Jochen,Van Poecke, Sara,Goeman, Jan,Henschker, Dajana,Beck, Edwald,Jomaa, Hassan,Van Calenbergh, Serge
, p. 1888 - 1891 (2007/10/03)
In view of the promising antimalarial activity of fosmidomycin or its N-acetyl homologue FR900098, the objective of this work was to investigate the influence of aromatic substituents in the α-position of the phosphonate moiety. The envisaged analogues we
