7749-92-0Relevant 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
, 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.
Synthesis of oxazinyl analogues of fosmidomycin using RCM methodology
Van Der Jeught, Sarah,Stevens, Christian V.,Dieltiens, Nicolai
, p. 3183 - 3187 (2008/09/19)
Fosmidomycin is a promising antimalarial compound with a novel mode of action, the inhibition of 1-deoxy-D-xylulose 5-phosphate reductoisomerase, a key enzyme in the biosynthesis of isoprenoids through the nonmevalonate pathway. This paper describes the synthesis of a series of analogues in which the hydroxamate moiety is incorporated in a ring structure, leaving the complexation with the enzyme up to the oxygen lone pairs instead of the free hydroxyl group. The antimalarial activities of the different analogues are currently under investigation. Georg Thieme Verlag Stuttgart.
ORGANOPHOSPHORIC DERIVATIVES USEFUL AS ANTI-PARASITIC AGENTS
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Page/Page column 31, (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-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
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
One-pot tandem 1,4-1,2-addition of phosphites to α,β-unsaturated imines for the synthesis of glutamic acid analogues
Moonen, Kristof,Van Meenen, Ellen,Verwee, Annelies,Stevens, Christian V.
, p. 7407 - 7411 (2007/10/03)
(Chemical Equation Presented) Evidently so: New mechanistic findings indicate that addition of dialkyl trimethylsilyl phosphites to α,β-unsaturated imines has been incorrectly reported as an exclusive 1,2-addition. When α,β-unsaturated imines are used as
A New and Easy Synthesis of Diethyl 2-Formylalkylphosphonates
Teulade, Marie-Paule,Savignac, Philippe
, p. 1037 - 1039 (2007/10/02)
Aldimines obtained from 2-alkenals are condensed with triethyl phosphite in ethanol in the presence of formic acid to give diethyl iminoalkylphosphonates; these are readily converted into diethyl formylalkylphosphonates in acidic medium.
