16165-66-5Relevant academic research and scientific papers
Phosphonate inhibitors of antigen 85C, a crucial enzyme involved in the biosynthesis of the Mycobacterium tuberculosis cell wall
Gobec, Stanislav,Plantan, Ivan,Mravljak, Janez,Wilson, Rosalind A.,Besra, Gurdyal S.,Kikelj, Danijel
, p. 3559 - 3562 (2004)
The first phosphonate inhibitors of antigen 85C - a major protein component of the Mycobacterium tuberculosis cell wall possessing mycolyltransferase activity were prepared using structure-based design. These potential novel antituberculosis agents, consisting of a phosphonate moiety, hydrophobic alkyl chain and a simple trehalose-mimicking aromatic structure, were designed as tetrahedral transition-state analogue inhibitors of antigen 85C, which catalyzes the key mycolyltransferase reaction involved in cell wall biosynthesis.
Synthesis and polymerization kinetics of acrylamide phosphonic acids and esters as new dentine adhesives
Besse,Le Pluart,Cook,Pham,Madec
, p. 149 - 157 (2013)
In restorative dentistry, acrylamide monomers bearing phosphonic acid moieties have proved to be useful species for the formulation of dental self-etch adhesives since they provide enhanced adhesion to hydroxyapatite and are not subject to hydrolysis, thus potentially improving their adhesive durability. Previous studies have demonstrated that phosphonic acid acrylamides increase the rate of photopolymerization of diacrylamide monomers. To understand whether this rate acceleration is specific to the acrylamide function of the monomer, or due to the phosphonic acid group per se, or is applicable only with a crosslinking reaction, we have synthesized several acrylamide and methacrylate monomers bearing phosphonic acid or phosphonate moieties and studied their photopolymerization kinetics. The acrylamide phosphonic acid was found to accelerate the polymerization rate but similar monomers bearing a phosphonate ester group had a much smaller effect. A similar accelerating effect was observed when the phosphonic acid-based monomers were copolymerized with a monofunctional acrylamide monomer, excluding the possibility that the rate acceleration might be related to the crosslinking process. This rate effect is also observed when a nonpolymerizable organic phosphonic acid is present in the polymerizing medium. We suggest that the increase of the medium polarity is responsible for this rate enhancement effect.
Conjugate Addition of Alkyl- and Vinyl-copper Complexes to α,β-Unsaturated Phosphonic Esters. Stereospecific Syntheses of γ,δ-Unsaturated Phosphonates
Nicotra, Francesco,Panza, Luigi,Russo, Giovanni
, p. 5 - 6 (1984)
Alkylcopper complexes add to diethyl ethenylphosphonate to afford phosphonic esters with the alkyl chain increased by two carbon atoms; analogously vinylcopper complexes afford γ,δ-unsaturated phosphonic esters with retention of configuration in the double bond.
Rotational Motions in n-Hexane Phosphonic Acid Diethyl Ester Studied Combining 2H, 13C, and 31P NMR. Analysis of the Phosphorus-31 Spin-Lattice Relaxation
Petr, A.,Grossmann, G.,Klose, G.,Ahlnaes, T.,Goetze, T.
, p. 231 - 242 (1986)
Spin-lattice relaxation of 13C and 31P in neat H3C(CH2)5P(O)(OC2H5)2 and of 2H and 31P in H3C(CH2)4C 2H2P(O)(OC2H5)2 and H3C(CH2)5P(O)(OC2 2H5)2 have been measured in the temperature range from - 70 to 160 deg C and at different fields.By using the NOE and the selectivity deuterated compounds the contributions of different segments to the total proton-phosphorus dipole-dipole relaxation were determined.Quantitative analysis of the 31P relaxation yields the result that, at the phosphorus resonance frequencies of 36.44 and 145.76 MHz and at all temperatures studied, at least two interaction mechanisms contribute.Further, the α-CH2 segment, the ester groups, and the hexyl residue without the α-CH2 segment, each gives approximately one-third of the total proton-phosphorus dipole-dipole contribution.The spin-lattice relaxation of 2H, 13C, and 31P is described on the basis of the Woessner model in the whole temperature range studied with one set of motional parameters.The relaxations of the spins in the H2CP(O)O2 and 2H2CP(O)O2 segments are mainly determined by the overall reorientation whereas this motion has at most a small effect on the 13C relaxation of the other segments and on the 2H relaxation of the ester groups.
Selective esterification of phosphonic acids
Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
, (2021/09/27)
Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.
Direct conversion of phosphonates to phosphine oxides: An improved synthetic route to phosphines including the first synthesis of methyl JohnPhos
Kendall, Alexander J.,Salazar, Chase A.,Martino, Patrick F.,Tyler, David R.
supporting information, p. 6171 - 6178 (2015/02/19)
The synthesis of tertiary phosphine oxides from phosphonates was achieved reliably and in good to excellent yields using stoichiometric amounts of alkyl or aryl Grignard reagents and sodium trifluoromethanesulfonate (NaOTf). In the absence of the NaOTf additive, covalent coordination oligomers of magnesium and phosphorus species dominate the reaction, producing very low yields of phosphine oxide, but high conversions of the phosphonate starting material. Mechanistic studies revealed that a five-coordinate phosphorus species - not a phosphinate - is the reaction intermediate. A diverse array of phosphonates was converted to phosphine oxides using a variety of Grignard reagents for direct carbon-phosphorus functionalization. This new methodology especially simplifies the synthesis of dimethylphosphino (RPMe2)-type phosphines by using air-, water-, and silica-stable intermediates. To highlight this reaction, a new Buchwald-type ligand ([1,1′-biphenyl]-2-yldimethylphosphine, or methyl JohnPhos) and a classic bidentate phosphine, bis(diphenylphosphino)propane (dppp), were synthesized in excellent yields.
Organic Compounds
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Page/Page column 7, (2010/05/13)
Disclosed are compounds having the ability to inhibit cytochrome P450 2A6, 2A13, and/or 2B6 and tobacco products comprising them. Also disclosed are pharmaceutical compositions comprising them.
ORGANIC COMPOUNDS
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Page/Page column 25, (2008/12/04)
Disclosed are compounds having the ability to modulate, namely to improve, enhance and or modify fragrance compositions due to their ability to inhibit cytochrome P450 enzymes, e.g. CYP2A13 and CYP2B6.
Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall
Gobec, Stanislav,Plantan, Ivan,Mravljak, Janez,Svajger, Urban,Wilson, Rosalind A.,Besra, Gurdyal S.,Soares, Sousana L.,Appelberg, Rui,Kikelj, Danijel
, p. 54 - 63 (2007/10/03)
Phosphonate inhibitors of antigen 85C were prepared. The inhibitors, comprising a phosphonate moiety, mycolic acid mimetic and a trehalose surrogate, contain substituted benzyl alcohols, N-(ω-hydroxyalky)phthalimide, 2-phenylethanol or 4-(phthalimido)butanol as trehalose mimetics, and an alkyl chain of different lengths mimicking the mycolic acid side chain. The best compounds inhibited the mycolyltransferase activity of antigen 85C with IC50 in the low micromolar range and inhibited the growth of Mycobacterium avium in culture. The best compounds in the 3-phenoxybenzyl- and ω-(phthalimido)alkoxy series, ethyl 3-phenoxybenzyl butylphosphonate (4a) and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl heptylphosphonate (5c) displayed IC50 values of 2.0 and 1.3 μM, respectively, in a mycolyltransferase inhibition assay. In a M. avium growth inhibition assay MIC of 4a and (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl ethyl nonylphosphonate (5d) were 248.8 and 84.5 μg/mL, respectively.
A new, effective approach for the C-C bond formation utilizing 1-, 2- and 3-phosphonyl substituted radicals derived from iodoalkylphosphonates and n-Bu3SnH/Et3B/O2 system
Balczewski,Pietrzykowski
, p. 7291 - 7304 (2007/10/03)
A new, practical synthesis of highly substituted phosphonates utilizing 1-, 2- and 3-phosphonyl substituted radicals derived from iodoalkylphosphonates and a catalytic or stoichiometric amounts of the n-Bu3SnH/Et3B/O2 reagent is described.
