3986-95-6Relevant academic research and scientific papers
Grafting of phosphonate groups onto PVA by acetalyzation. Evaluation of the anti-corrosive properties for the acetalyzed PVA coatings
David, Ghislain,Ortega, Esteban,Chougrani, Kamel,Manseri, Abdelatif,Boutevin, Bernard
, p. 599 - 606 (2011)
One novel aldehyde bearing a phosphonate group, ca. (3-diethylphosphonate) propanal, was successfully synthesized and characterized by means of NMR. Then phosphonic acid ester groups were chemically grafted onto poly(vinyl acetal) pre-made polymers, and especially poly(vinyl butyral) (PVB). Four acetalyzed PVA were then synthesized with different molar contents of either butyral or (3-diethylphosphonate)propanal groups. Only PVAP4 was composed of both groups, i.e. 80 mol% of butyral and 20 mol% of phosphonate. TGA of acetalyzed PVA showed a clear improvement of the PVA thermal stability. Furthermore, for PVAP3, having 50 mol% of phosphonate groups, 40% of weight remained after 600 °C under air. This high thermostability was attributed to stable anhydride bonds. Finally, the coatings were subject to the salt spray test for duration up to 120 h. The results indicate that PVAP3 coating shows an excellent resistance to corrosion, thus excellent adhesive properties, as no corrosion was observed until 100 h subject to the salt spray test.
Phosphonic derivatives of carbohydrates: Chemoenzymatic synthesis
Guanti, Giuseppe,Banfi, Luca,Zannetti, Maria Teresa
, p. 3181 - 3185 (2000)
A series of homologous racemic β-hydroxyaldehydes bearing a phosphonate group in the ω-position were synthesised and allowed to react with dihydroxyacetone phosphate (DHAP) via an enzymatic aldol addition catalysed by fructose 1,6-bisphosphate aldolase (FruA). After enzymatic dephosphorylation, a set of unnatural ω-phosphonic deoxysugars was obtained. (C) 2000 Elsevier Science Ltd.
Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase
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Page/Page column 43; 44; 48; 49; 50, (2017/04/11)
In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or (II) where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).
Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase
Clinch, Keith,Crump, Douglas R.,Evans, Gary B.,Hazleton, Keith Z.,Mason, Jennifer M.,Schramm, Vern L.,Tyler, Peter C.
, p. 5629 - 5646 (2013/09/02)
The pathogenic protozoa responsible for malaria lack enzymes for the de novo synthesis of purines and rely on purine salvage from the host. In Plasmodium falciparum (Pf), hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT) converts hypoxanthine to inosine monophosphate and is essential for purine salvage making the enzyme an anti-malarial drug target. We have synthesized a number of simple acyclic aza-C-nucleosides and shown that some are potent inhibitors of Pf HGXPRT while showing excellent selectivity for the Pf versus the human enzyme.
Design of potential bisubstrate inhibitors against Mycobacterium tuberculosis (Mtb) 1-deoxy-d-xylulose 5-phosphate reductoisomerase (Dxr)-evidence of a novel binding mode
San Jose, Geraldine,Jackson, Emily R.,Uh, Eugene,Johny, Chinchu,Haymond, Amanda,Lundberg, Lindsay,Pinkham, Chelsea,Kehn-Hall, Kylene,Boshoff, Helena I.,Couch, Robin D.,Dowd, Cynthia S.
, p. 1099 - 1104 (2013/07/26)
In most bacteria, the nonmevalonate pathway is used to synthesize isoprene units. Dxr, the second step in the pathway, catalyzes the NADPH-dependent reductive isomerization of 1-deoxy-d-xylulose-5-phosphate (DXP) to 2-C-methyl-d-erythritol-4-phosphate (MEP). Dxr is inhibited by natural products fosmidomycin and FR900098, which bind in the DXP binding site. These compounds, while potent inhibitors of Dxr, lack whole cell activity against Mycobacterium tuberculosis (Mtb) due to their polarity. Our goal was to use the Mtb Dxr-fosmidomycin co-crystal structure to design bisubstrate ligands to bind to both the DXP and NADPH sites. Such compounds would be expected to demonstrate improved whole cell activity due to increased lipophilicity. Two series of compounds were designed and synthesized. Compounds from both series inhibited Mtb Dxr. The most potent compound (8) has an IC50 of 17.8 μM. Analysis shows 8 binds to Mtb Dxr via a novel, non-bisubstrate mechanism. Further, the diethyl ester of 8 inhibits Mtb growth making this class of compounds interesting lead molecules in the search for new antitubercular agents.
COMPOUNDS FOR INHIBITING 1- DEOXY-D-XYLULOSE- 5 - PHOSPHATE REDUCTOISOMERASE
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Paragraph 0065; 0067, (2013/03/26)
[0082] In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits l-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).
Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents
Ponaire, Sarah,Zinglé, Catherine,Tritsch, Denis,Grosdemange-Billiard, Catherine,Rohmer, Michel
experimental part, p. 277 - 285 (2012/07/14)
Since Mycobacterium tuberculosis sets up several multiple anti-tuberculosis drug resistance mechanisms, development of new drugs with innovative target is urgent. The methylerythritol phosphate pathway (MEP) involved in the biosynthesis of essential metab
Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR)
Zingle, Catherine,Kuntz, Lionel,Tritsch, Denis,Grosdemange-Billiard, Catherine,Rohmer, Michel
supporting information, p. 6563 - 6567,5 (2012/12/12)
Fosmidomycin derivatives in which the hydroxamic acid group has been replaced by several bidentate chelators as potential hydroxamic alternatives were prepared and tested against the DXR from Escherichia coli. These results illustrate the predominant role
Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR)
Zinglé, Catherine,Kuntz, Lionel,Tritsch, Denis,Grosdemange-Billiard, Catherine,Rohmer, Michel
supporting information, p. 6563 - 6567 (2013/01/14)
Fosmidomycin derivatives in which the hydroxamic acid group has been replaced by several bidentate chelators as potential hydroxamic alternatives were prepared and tested against the DXR from Escherichia coli. These results illustrate the predominant role
PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND USES THEREOF
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Page/Page column 44-45, (2012/11/14)
The invention relates to compounds of formula (I) that are inhibitors of hypoxanthine and/or guanine purine phosphoribosyltransferases and to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and methods of treating diseases or conditions in which it is desirable to inhibit hypoxanthine and/or guanine purine phosphoribosyltransferases. Such diseases include malaria.
