- Tetra-Substituted p-Tert-Butylcalix[4]Arene with Phosphoryl and Salicylamide Functional Groups: Synthesis, Complexation and Selective Extraction of f-Element Cations
-
A new series of lanthanide (1–5) and uranyl (6) complexes with a tetra-substituted bifunctional calixarene ligand H2L is described. The coordination environment for the Ln3+ and UO22+ ions is provided by phosphoryl and salicylamide functional groups appended to the lower rim of the p-tert-butylcalix[4]arene scaffold. Ligand interactions with lanthanide cations (light: La3+, Pr3+; intermediate: Eu3+ and Gd3+; and heavy: Yb3+), as well as the uranyl cation (UO22+) is examined in the solution and solid state, respectively with spectrophotometric titration and single crystal X-ray diffractometry. The ligand is fully deprotonated in the complexation of trivalent lanthanide ions forming di-cationic complexes 2 : 2 M : L, [Ln2(L)2(H2O)]2+ (1–5), in solution, whereas uranyl formed a 1 : 1 M : L complex [UO2(L)(MeOH)]∞ (6) that demonstrated very limited solubility in 12 organic solvents. Solvent extraction behaviour is examined for cation selectivity and extraction efficiency. H2L was found to be an effective extracting agent for UO22+ over La3+ and Yb3+ cations. The separation factors at pH 6.0 are: βUO (Formula presented.) /La (Formula presented.) =121.0 and βUO (Formula presented.) /Yb (Formula presented.) =70.0.
- Glasneck, Florian,Kersting, Berthold,Roode-Gutzmer, Quirina I.,Stumpf, Thorsten
-
supporting information
(2022/02/02)
-
- The hydrophilizing agent for producing a self-emulsifiable polyisocyanate composition, a self-emulsifiable polyisocyanate compositions and coating composition (by machine translation)
-
[A] a self-emulsifiable polyisocyanate composition has excellent adhesion to the substrate of a metal such as aluminum. (A) a compound represented by the formula [a] 1 anionic and, (b) organic polyisocyanate, and (c) a self-emulsifiable polyisocyanate com
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-
Paragraph 0092
(2020/12/30)
-
- IONIC LIQUID
-
Ionic liquids are described which have a very broad electrochemical stability window and which are therefore of high utility for a wide range of electrochemical energy storage device applications.
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Page/Page column 40; 41
(2019/05/15)
-
- Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds
-
Phosphonates have garnered considerable attention for years owing to both their singular biological properties and their synthetic potential. State-of-the-art methods for the preparation of mixed phosphonates, phosphonamidates, phosphonothioates, and phos
- Adler, Pauline,Pons, Amandine,Li, Jing,Heider, J?rg,Brutiu, Bogdan R.,Maulide, Nuno
-
supporting information
p. 13330 - 13334
(2018/09/25)
-
- Synthesis and biological activity investigation of azole and quinone hybridized phosphonates
-
Phosphonates, azoles and quinones are pharmacophores found in bioactive compounds. A series of phosphonates conjugated to azoles and quinones with variable carbon chain lengths were synthesized in 3–4 steps with good yield. Antifungal assay of these compounds showed that ethyl protected phosphates have excellent inhibitory activity against phytopathogenic fungus Fusarium graminearum, and the free-base phosphates have good activity against human pathogenic fungi Aspergillus flavus and Candida albicans. Structure- activity relationship (SAR) studies showed activity increases with longer carbon chain length between phosphonate and anthraquinone analogs consisting of azole and quinone moieties. These newly synthesized compounds also have mild antibacterial activities to Gram positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). Cytotoxicity analysis of these compounds against HeLa cells reveals that the phosphoric acid analogs are less toxic compared to ethyl protected phosphonates. Three leads compounds have been identified with prominent antifungal activity and low cytotoxicity.
- Subedi, Yagya Prasad,Alfindee, Madher N.,Shrestha, Jaya P.,Becker, Greg,Grilley, Michelle,Takemoto, Jon Y.,Chang, Cheng-Wei Tom
-
supporting information
p. 3034 - 3037
(2018/08/09)
-
- Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase
-
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).
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Page/Page column 41; 42; 43; 44
(2017/04/11)
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- ENOLASE INHIBITORS AND METHODS OF TREATMENT THEREWITH
-
Provided herein are compounds of the formula (I) wherein the variables R1, R2, R3, R4, X1, X2, Y1, and A1 are as defined herein. Such compounds may be used, for exampl
- -
-
Paragraph 00157
(2016/09/26)
-
- COMPOUND, SURFACE TREATMENT AGENT, AND SURFACE TREATMENT METHOD
-
PROBLEM TO BE SOLVED: To provide a novel compound which is suitable for use as a surface treatment agent and has high stability, a surface treatment agent containing the compound, and a surface treatment method. SOLUTION: The compound is represented by formula (I) (R1 to R4 are each independently H, an alkyl group, or an alkoxy group which may have a perfluoroalkyl group as a substituent; R5 is H or a C1-6 alkyl group which may have a halogen atom as a substituent; X is a group represented by -OCONH-, -OCOS-, -OCOO-, -NH-, -S-, -O-, or -OCO-; when X is other than -OCO-, R6 is an alkylene group; and when X is -OCO-, R6 is a single bond or an alkylene group). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT
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-
Paragraph 0137; 0138
(2017/07/25)
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- Co(II)4Gd(III)6 phosphonate grid and cage as molecular refrigerants
-
The study on structure-property relationships of polynuclear 3d-Gd clusters are very essential in the fields of magnetic refrigerants. We designed two new bulky phosphonic acids: (3-(9H-carbazol-9-yl)propyl)phosphonic acid (CarbpPO3H2) and (2-(9-methyl-9H-fluoren-9-yl)ethyl)phosphonic acid (FlumePO3H2). Based on these ligands, two clusters [Co(II)4Gd(III)6(CarbpPO3)6(tBuCO2)14(tBuCO2H)(H2O)3].9CH3CN.CH2Cl2 (1) and [Co(II)4Gd(III)6(FlumePO3)3(tBuCO2)14(μ3-OH)6(H2O)2(CH3CN)].6CH3CN (2) were synthesized under ambient condition. Compound 1 has a [3 × 3] grid-like structure, while compound 2 has a rare helmet-like cage structure. The magnetocaloric effect (MCE) have been tuned from 22.83 to 29.06 J kg-1 K-1 as the molecular structure changes from grid to cage.
- Tang, Xiaoyan,Zhong, Qixuan,Xu, Ji,Li, Haiqing,Xu, Sinong,Cui, Xueyuan,Wei, Bo,Ma, Yunsheng,Yuan, Rongxin
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supporting information
p. 195 - 199
(2016/01/12)
-
- An efficient nonconventional glycerol-based solid acid catalyzed synthesis and biological evaluation of phosphonate conjugates of 1,2,4-triazole thiones
-
A series of diethyl (3-((5-aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phos-phonates (7a-t) has been synthesized in excellent yields by coupling diethyl (3-bromopropyl)phosphonate and 5-aryl-1H- 1,2,4-triazol-3-thiones employing an efficient, green and nonconventional heterogeneous SO3Hcarbon catalyst derived from glycerol. In addition, a facile and green approach for the esterification of carboxylic acids by utilizing glycerol-based solid acid catalyst has been reported. Structures of the synthesized compounds were characterized by IR, NMR and HRMS studies. These triazole derivatives were screened for their in vitro cytotoxicity using the standard MTT (3-(4,5-dimethylthiazol-2- yl)-2,5-diphenyltetra-zolium bromide) assay against a panel of five different human cancer cell lines (HeLa: Cervix, A549: Lung, A375: Skin, MDA-MB-231: Breast and T98G: Brain). The antimicrobial activities of the synthesized compounds were investigated against four bacterial strains: Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and three fungal strains: Aspergillus Niger, Aspergillus terreus, Aspergillus fumigatus. Preliminary results indicate that the compound 7f displayed maximum anticancer activity and the compounds 7d, 7e, 7f, 7m and 7q exhibited moderate antibacterial activity. The compounds 7g, 7h, 7o and 7p showed good antifungal activity with high inhibition zone diameter compared to the standard drug.
- Murty, Madugula S.R.,Katiki, Mohana R.,Rao, Busam R.,Narayanan, Sai S.,Anto, Ruby J.,Buddana, Sudhreer K.,Prakasham, Reddy S.,Devi, Bethala L.A.P.,Prasad, Rachapudi B.N.
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p. 968 - 981
(2016/10/31)
-
- Synthesis of advanced fluorescent probes — water-soluble symmetrical tricarbocyanines with phosphonate groups
-
A method for the synthesis of a series of water-soluble heptamethine indocyanine dyes containing a phosphonate group in the substituent bonded to the quaternary nitrogen atom of the indolenine moiety has been developed.
- Podrugina,Temnov,Doroshenko,Kuzmin,Nekipelova,Proskurnina,Zefirov
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p. 2722 - 2728
(2017/05/19)
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- A rhodium triphenylphosphine catalyst for alkene hydrogenation supported on neat superparamagnetic iron oxide nanoparticles
-
A phosphonic acid functionalized triphenylphosphine rhodium complex was synthesized and grafted onto neat superparamagnetic iron oxide nanoparticles. The material was investigated by elemental analysis, IR spectroscopy, thermogravimetric analysis, XRD, N2-physisorption analyses, and TEM measurements. The obtained hybrid material could be used as a catalyst for the hydrogenation of alkenes with excellent yields and a broad substrate scope. The catalyst can be reused ten times without any loss of activity. According to the results from X-ray absorption spectroscopy, it is likely that formation of Rh nanoparticles occurs during the reaction.
- Dehe, Daniel,Wang, Lei,Müller, Melanie K.,D?rr, Gunder,Zhou, Zhou,Klupp-Taylor, Robin N.,Sun, Yu,Ernst, Stefan,Hartmann, Martin,Bauer, Matthias,Thiel, Werner R.
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p. 127 - 136
(2015/03/05)
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- PHOSPHORUS FUNCTIONAL ANTIMICROBIAL COATINGS FOR METAL SURFACES
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The invention relates to quaternary ammonium multi-dentate mono-, bis-, tris- and tetrakis-phosphonate compounds, processes for preparing quaternary ammonium multi-dentate mono-, bis-, tris- and tetrakis-phosphonate compounds, antimicrobial coating compositions comprising quaternary ammonium multi-dentate mono-, bis-, tris- and tetrakis-phosphonate compounds and method of treating a surface with said compositions to provide a durable, antimicrobial-treated surface.
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Page/Page column 44
(2014/09/03)
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- ANTIDIABETIC TRICYCLIC COMPOUNDS
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Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.
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Page/Page column 184
(2014/02/16)
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- ANTIDIABETIC TRICYCLIC COMPOUNDS
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Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.
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Page/Page column 169
(2014/02/16)
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- Magnetically Recyclable Nano-Fe 2O 3-Catalyzed Chemoselective Synthesis and Antioxidant Activity of Diethyl (3-((5-Aryl-1 H-1,2,4-triazol-3-yl)thio)propyl) phosphonates
-
An efficient, green, and chemoselective S-alkylation of 5-aryl-1H-1,2,4-triazole-3-thiones with diethyl (3-bromopropyl)phosphonate in water, catalyzed by nano-Fe2O3 under ligand-and base-free conditions, is reported. Clean reaction, less expensive catalyst, excellent yields, and easy workup are the advantages of the present method. The catalyst can be easily collected by a magnet and recycled without significant loss in catalytic activity. The newly synthesized compounds were screened for their antioxidant property by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay. The majority of the compounds exhibited good antioxidant activity.
- Murty,Katiki, Mohana Rao,Rao, B. Ramalingeswara,Nanubolu, Jagadeesh Babu,Buddana, Sudheer Kumar,Prakasham
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p. 2724 - 2737
(2014/08/18)
-
- Design of potential bisubstrate inhibitors against Mycobacterium tuberculosis (Mtb) 1-deoxy-d-xylulose 5-phosphate reductoisomerase (Dxr)-evidence of a novel binding mode
-
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.
- 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.
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supporting information
p. 1099 - 1104
(2013/07/26)
-
- COMPOUNDS FOR INHIBITING 1- DEOXY-D-XYLULOSE- 5 - PHOSPHATE REDUCTOISOMERASE
-
[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).
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-
Paragraph 0065; 0066
(2013/03/26)
-
- A novel click-chemistry approach to flame retardant polyurethanes
-
The low thermo-oxidative properties of PU foams somewhat limits their practical application, particularly as heat sensitive materials. The introduction of a covalently linked flame retardant organophosphonate ester into the PU foam was achieved using the
- Borreguero, Ana M.,Sharma, Pallavi,Spiteri, Christian,Velencoso, María M.,Carmona, Manuel S.,Moses, John E.,Rodríguez, Juan F.
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p. 1207 - 1212
(2013/10/22)
-
- Synthesis and characterization of aminophosphonates zirconium as new mesoporous materials
-
A serial of aminophosphonates zirconium with the different arm lengths of -(CH2)n- organic chains (n=2-6) was synthesized for the first time. These compounds are characterized by FT-IR, SEM, TEM, TG and nitrogen adsorption-desorption. And based on the experimental data, these materials not only have layer structure mesoporous and good thermal stability such as zirconium phosphate, but also can be adjusted the layer distance, pore size and pore volume. So aminophosphonates zirconium posses special excellent properties and will have potential prospect applications.
- Zhou, Liang
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experimental part
p. 1320 - 1326
(2012/05/21)
-
- ω-haloalkylphosphoryl compounds: Synthesis and properties
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A general method of the synthesis of ω-haloalkylphosphoryl compounds was developed, a series of compounds of phosphonic and phosphine oxide type were synthesized. The ability of some ω-haloalkylphosphonates to undergo intramolecular cyclization into the corresponding 1,2-oxaphospholane and 1,2-oxaphosphorine was investigated depending on the solvent polarity, the presence of halogen ions in the solution, and temperature. Tetrahydrofuran was chosen as one of the most suitable solvents for the alkylation of CH acids with ω-haloalkylphosphoryl compounds.
- Ragulin
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p. 1928 - 1937
(2013/06/05)
-
- Synthesis of ω-phthalimidoalkylphosphonates
-
A series of carbon chain growing ω-phthalimidoalkylphosphonates was prepared from simple and easy available raw materials by twostep reaction. The yields can reach 58 %-64 %. Their structures are confirmed by 1H NMR correctly.
- Zhou, Liang
-
experimental part
p. 4821 - 4822
(2012/08/14)
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- Studies on the synthesis of a chiral salen Mn (III) complex immobilised onto zirconium aminophosphonates and catalytic asymmetric epoxidation of α-methylstyrene
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A chiral salen Mn (III) complex has been immobilised onto zirconium aminophosphonates by axial coordination with different linkage arm lengths (CH2)n (n = 2-6), to give a series of heterogeneous catalysts. The catalysts exhibited good to excellent catalytic efficiency in the asymmetric epoxidation of α-methylstyrene. One heterogeneous catalyst, with n = 6, gave higher catalytic properties than the original chiral salen Mn (III) complex in the NaClO/PPNO system. It can be easily recovered and reused several times without significant loss of activity.
- Zhou, Liang
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p. 512 - 515
(2012/10/29)
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- Photopolymerization of self-assembled monolayers of diacetylenic alkylphosphonic acids on group-III nitride substrates
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This paper describes the fabrication and characterization of photopolymerizable alkylphosphonate self-assembled monolayers (SAMs) on group-III nitride substrates including GaN and AlxGa1-xN (AlGaN; x = 0.2 and 0.25). Contact angle goniometry, visible absorption spectroscopy, and atomic force microscopy were used to assess the formation, desorption, and photopolymerization of SAMs of diacetylenic alkylphosphonic acids (CH3(CH2)n-C≡C-C≡C-(CH 2)mPO(OH)2; (m, n) = (3, 11), (6, 8), and (9, 5)). As with GaN substrates (Ito, T.; Forman, S. M.; Cao, C.; Li, F.; Eddy, C. R., Jr.; Mastro, M. A.; Holm, R. T.; Henry, R. L.; Hohn, K.; Edgar, J. H. Langmuir 2008, 24, 6630-6635), alkylphosphonic acids formed SAMs on UV/O 3-treated AlGaN substrates from their toluene solutions in contrast to other primary substituted hydrocarbons with a terminal -COOH, -NH 2, -OH, or -SH group. Diacetylenic alkylphosphonate SAMs on group-III nitrides could be polymerized by UV irradiation (254 nm), as indicated by the appearance of a visible absorption band around 640 nm and also by their significantly reduced desorption from the surface in a 0.1 M aqueous NaOH solution. A longer UV irradiation time was required to maximize the photopolymerization of a SAM having a diacetylene group close to the terminal phosphonate moiety, probably because of the hindrance of the topochemical polymerization due to the limited flexibility of the cross-linking moieties on an atomically rough substrate surface.
- Li, Feng,Shishkin, Evgeniy,Mastro, Michael A.,Hite, Jennifer K.,Eddy, Charles R.,Edgar,Ito, Takashi
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experimental part
p. 10725 - 10730
(2011/02/16)
-
- PROCESS FOR PREPARING MATERIALS BY GRAFTING HALOGENATED PHOSPHORUS-CONTAINING GROUPS ONTO AN INORGANIC SURFACE
-
The invention concerns a process for preparing a hybrid organic-inorganic material (HOIM) with phosphorus-containing bridges between the surface of an inorganic substrate containing an element M and one or more organic groups of the covalent M-O-P-R type, said process using, as a precursor for said organic group or groups, at least one organophosphorus acid halide with formula RxP(O)Xy in which x=1 or 2, y=3?x, X being a halogen and R designating at least one organic alkyl, aryl or aryl-alkyl group. Non-exhaustive applications for the hybrid organic-inorganic material obtained by the process of the invention are in the fields of anti-corrosion, lubrication, microelectronics, nanotechnologies, composite materials, heterogeneous catalysis, supported catalysis, depollution and biomedical applications.
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Page/Page column 4
(2010/04/23)
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- PREPARATION OF AN INORGANIC SUBSTRATE HAVING ANTIMICROBIAL PROPERTIES
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The invention relates to a process for modifying an inorganic substrate, directed toward giving it antimicrobial properties, said process consisting in grafting in one or more steps onto a surface of said substrate groups with intrinsic antimicrobial properties or groups capable of releasing species with antimicrobial properties. The grafting is performed by means of an organophosphorus coupling agent. A subject of the invention is similarly a substrate obtained by this process, as well as diverse uses of such a substrate.
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Page/Page column 5
(2010/10/19)
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- Reaction of dibromoalkanes with silyl phosphites. Synthesis and properties of mono-and diphosphonoalkanes
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Reactions of dibromoethane and dibromopropane with silyl phosphites are studied. Mono-and diphosphonoalkanes of various structures were prepared, and their chemical properties were studied. Pleiades Publishing, Inc., 2006.
- Pudovik,Terent'eva,Kibardina,Pudovik
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p. 714 - 719
(2008/02/02)
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- Allosteric effects in asymmetric hydrogenation catalysis? Asymmetric induction as a function of the substrate and the backbone flexibility of C 1-symmetric diphosphines in rhodium-catalysed hydrogenations
-
The new unsymmetrical, optically active ligands 1,2-C2H 4(PPh2)(2′R,5′R-2′,5′- dimethylphospholanyl) (La) and 1,3-C3H 6(PPh2)(2′R,5′R-2′,5′- dimethylphospholanyl) (Lb) form complexes of the type [Rh(L)(cyclooctadiene)][BF4] where L = La (1a) or L b (1b), [PtCl2(L)] where L = La (2a) or L b (2b) and [PdCl2(L)] where L = La (3a) or Lb (3b). The crystal structures of 2a and 2b show the chelate ligand backbones adopt δ-twist and flattened chair conformations respectively. Asymmetric hydrogenation of enamides and dehydroaminoesters using 1a and 1b as catalysts show that the ethylene-backboned diphosphine La gives a more efficient catalyst in terms of asymmetric induction than the propylene-backboned analogue Lb. The greatest enantioselectivities were obtained with 1a and enamide substrates with ees up to 91%. Substrate-induced conformational changes in the Rh-diphosphine chelates are proposed to explain some of the ees observed in the hydrogenation of enamides. The Royal Society of Chemistry 2006.
- Baber, Angharad,De Vries, Johannes G.,Orpen, A. Guy,Pringle, Paul G.,Von Der Luehe, Karl
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p. 4821 - 4828
(2007/10/03)
-
- Materials comprising organic groups containing sulphur and phosphorous bonded to a mineral oxide via oxygen atoms
-
The invention describes materials comprising organic groups containing sulphur and phosphorous bonded together by a hydrocarbon chain and bonded via phosphorous and oxygen atoms to a mineral oxide of an element M, said materials being characterized in that they comprise M-O-M′ bonds, M′representing an element of a mineral oxide identical to or different from M, in that the ratio of the element M to the phosphorous is about 0.5: 1 to about 500:1 and in that each phosphorous atom of the phosphorous-containing groups forms at least one P—O-M bond and/or P—O-M′ bond. The invention also describes a process for preparing such materials.
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Page/Page column 2
(2008/06/13)
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- Use of organophosphorus compounds for the therapeutic and prophylactic treatment of infections
-
Use of organophosphorus compounds of general Formula (I) for the therapeutic and prophylactic treatment of infections in humans and animals caused by viruses, fungi and parasites.
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Page column 13, 14
(2010/02/05)
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- Diaryl ester prodrugs of FR900098 with improved in vivo antimalarial activity
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The fosmidomycin derivative FR900098 represents an inhibitor of the 1-deoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase with potent antimalarial activity. Prodrugs of FR900098 with increased activity after oral administration were obtained by chemical modification of the phosphonate moiety to yield phosphodiaryl esters. One diaryl ester prodrug demonstrated efficacy in mice infected with the rodent malaria parasite Plasmodium vinckei comparable to ip drug administration.
- Reichenberg, Armin,Wiesner, Jochen,Weidemeyer, Claus,Dreiseidler, Erhard,Sanderbrand, Silke,Altincicek, Boran,Beck, Ewald,Schlitzer, Martin,Jomaa, Hassan
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p. 833 - 835
(2007/10/03)
-
- Design and development of the first peptide-chelating bisphosphane bioconjugate from a novel functionalized phosphorus(III) hydride synthon
-
Remarkable oxidative stability is shown by the carboxylate- functionalized primary bisphosphane 1. Compound 1 can be used in conjugation reactions with biomolecules for functionalization through the COOH group without prior protection of PH2 groups. A novel water-soluble bisphosphane was obtained by reaction of the PH2 groups of 1 with formaldehyde under mild conditions.
- Gali, Hariprasad,Karra, Srinivasa R.,Reddy, V. Sreenivasa,Katti, Kattesh V.
-
p. 2020 - 2023
(2007/10/03)
-
- Long-Lived Photoinduced Charge Separation and Redox-Type Photochromism on Mesoporous Oxide Films Sensitized by Molecular Dyads
-
The photoinduced charge separation in three different assemblies composed of an electron donor D and a chromophore sensitizer S adsorbed on nanocrystalline TiO2 films (D-S|TiO2) was investigated. In all of the systems, the sensitizer was a ruthenium(II) bis-terpyridine complex anchored to the semiconductor surface by a phosphonate group. In two of the assemblies, the donor was a 4-(N,N-di-p-anisylamino) phenyl group linked to the 4′ position of the terpyridine, either directly (dyad D1-S) or via a benzyl ether interlocking group (dyad D2-S). In the third system, the sensitizer and the donor (3-(4-(N,N-di-p-anisylamino)phenoxy)-propyl-1-phosphonate) were coadsorbed on the surface ((D3+S)|TiO2). Laser flash photolysis showed that the photoinduced charge separation process follows the sequence D-S*|TiO2 1→ D-S+|(e-)TiO2 2→ D+-S|(e-)TiO2 3→ D-S|TiO2 Resonance Raman spectroscopy indicates that in the excited assemblies D2-S*|TiO2 and (D3+S*)|TiO2, one electron is promoted from the metal center to the terpyridine ligand linked to the semiconductor, whereas in the system D1-S*|TiO2 the excited electron is located on the ligand linked to the donor. The quantum yield of charge separation (steps 1 and 2) was found to be close to unity for the two former assemblies but only 60% for the latter one. In all three cases, the electron injection was very fast (++S)|(e-)TiO2, as in the model system S+|(e-)TiO2; it was 30 μs in D1+-S|(e-)TiO2 and 300 μs in D2+-S|(e-)TiO2. Electrodes made of any of the surface-confined dyads on conducting glass display a strong redox-type photochromism. When a positive potential (+0.5 V vs NHE) is applied to the electrode, charge recombination (step 3) is blocked. As a result, the visible absorption spectrum of the electrode changes, due to the appearance of the absorption feature of the oxidized donor (λmax = 730 nm). Return to the reduced state is achieved by electron injection through the conduction band of the TiO2 under forward bias (-0.5 V). None of the assemblies D1-S|TiO2 and D2-S|TiO2 gave better photovoltaic performances than the model system S|TiO2. This was attributed in the first case to the low injection efficiency and, in the second case, to an additional short-circuiting pathway constituted by the charge percolation inside the molecular monolayer and to the underlying conducting glass, as previously observed with monolayers of the donor D3 (Bonhote, P.; Gogniat, E.; Tingry, S.; Barbe, C.; Vlachopoulos, N.; Lenzmann, F.; Comte, P.; Graetzel, M. J. Phys. Chem. B 1998, 102, 1498-1507).
- Bonhote, Pierre,Moser, Jacques-E.,Humphry-Baker, Robin,Vlachopoulos, Nicolas,Zakeeruddin, Shaik M.,Walder, Lorenz,Graetzel, Michael
-
p. 1324 - 1336
(2007/10/03)
-
- Rapid and efficient Arbuzov reaction under microwave irradiation
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Diethyl alkylphosphonates are efficiently and rapidly prepared in good yields (75-99%) from trialkylphosphates and alkyl halides under short microwaves irradiations.
- Villemin, Didier,Simeon, Fabrice,Decreus, Hugues,Jaffres, Paul-Alain
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p. 209 - 213
(2007/10/03)
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- Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their use as pharmaceuticals
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Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their use as pharmaceuticals A compound of the formula STR1 where R1 and R3 are identical or different and at least one of the radicals R1 and R3 is a radical of the formula XI STR2 in which E is a covalent bond or a (C1 -C5)-alkyl, are suitable for the production of pharmaceuticals for the treatment of muscular atrophy, cachexia, muscular dystrophy, sepsis, septic shock, endotoxic shock, systemic inflammation response syndrome, adult respiratory distress syndrome, cerebral malaria, chronic pneumonia, pulmonary sarcoidosis, reperfusion damage, scar formation, inflammation of the bowel and ulcerative colitis, as a result of infections, acquired immune deficiency syndrome, cancer, trauma and other disorders having increased protein loss, peripheral circulatory disorders, disorders having altered leucocyte adhesion, and also disorders which are accompanied by an increased or unregulated tumor necrosis factor production such as rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis and other arthritic disorders.
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- Phosphorus-containing aminocarboxylic acids. VI. Improved synthesis of 2-amino-5-phosphonopentanoic acid
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An improved three-step procedure for the synthesis of 2-amino-5-phosphonopentanoic acid is proposed.
- Rozhko,Ragulin,Tsvetkov
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p. 1065 - 1067
(2007/10/03)
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- A free radical approach to functionalization of phosphonates utilizing novel 2- and 3-phosphonyl radicals
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A general method for the phosphonyl C2-C3-C bond formation under the free radical, reductive conditions is described. The new approach is based on the synthesis of novel 2- and 3-phosphonyl radicals 6, 9 derived from the corresponding 2- and 3-halo (X = Cl, Br, I) substituted phosphonates 7, 10 and their reaction with alkenes 4. Functionalized phosphonates 5, 8 possessing the 2+2 and 3+2 elongated carbon chain were obtained in 24-73% yields.
- Balczewski, Piotr,Pietrzykowski, Witold M.
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p. 13681 - 13694
(2007/10/03)
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- Highly enantioselective synthesis of (R)- and (S)-2-amino-5-phosphonopentanoic acids [(R)- and (S)-AP5] via modified Seebach imidazolidinones
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The preparation of four new stereoisomeric 1-carbobenzyloxy-2-tert-butyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-o nes is described. Alkylation of the lithium enolates of these chiral glycine derivatives proceeds with high diastereoselectivity. In particula
- Garcia-Barradas, Oscar,Juaristi, Eusebio
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p. 3423 - 3434
(2007/10/02)
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- Intramolecular Catalysis of Dialkyl ω-Aminoalkylphosphonate Hydrolysis
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The influence that intramolecular catalysis of hydrolysis of O-alkyl S-alkylphosphonothioates by amino groups may have on the product distribution of the reaction is investigated by study of a series of model compounds.The hydrolysis of diethyl phosphonates and diethyl phosphonates has been investigated at 75 deg C over the pH range 8.21-11.45.Contributions to hydrolysis of the ethoxy groups by intramolecular catalysis by the amino groups have been identified for - and -phosphonates.Secondary and tertiary amino groups assist hydrolysis through general base catalysis.An additional contribution to hydrolysis of the secondary amino compounds by intramolecular nucleophilic catalysis is also observed.
- Leslie, D. Ralph,Pantelidis, Sue
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p. 545 - 560
(2007/10/02)
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- Synthesis of acyclonucleoside phosphonates as antiviral agents against cytomegalovirus
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Phosphonic acid analogs of ACV and DHPG that are isosteric with ACV phosphate and DHPG phosphate have been synthesized and evaluated for antiviral activity against human, murine, and guinea pig strains of cytomegalovirus. The phosphonates showed high activity against all of the strains. They were also evaluated against a DHPG resistant strain of human cytomegalovirus. Although the activity dropped considerably, significant antiviral activity was still evident.
- Reist,Bradford III,Ruhland-Fritsch,Sturm,Zaveri,Huffman,Sidwell
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p. 539 - 550
(2007/10/02)
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- Synthesis of ω-phthalimidoalkylphosphonates
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Diethyl phthalimidoalkylphosphonates were synthesized by the reaction of diethyl bromoalkylphosphonates with N-(tert-butyldimethylsilyl)phthalimide in the presence of tetrabutylammonium fluoride.
- Chun,Park,Oh,Hong,Kim
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p. 909 - 910
(2007/10/02)
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- Syntheses de phosphobetaines amphiphiles neutres a distances intercharge variables
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Neutral amphiphilic phosphonato- and phosphinatobetaines having different interionic distances are synthesized.Two paths for this synthesis have been studied. 2-(Ethoxy or phenyl) 2-oxo 1,2-oxaphospholanes react with lipophilic tertiary amines at 150 deg C, giving rise to mixtures of phosphobetaines and oxaphospholanate ammonium salts.Lewis acids increase the reaction rate but cannot change the selectivity.The specific production of phosphobetaines is achieved by a three steps sequence: the Arbusov reaction is applied to α,ο-dibromoalcanes and triethylphosphite or phenyldiethylphosphonite, providing ο-bromophosphonates in high yield.Tertiary amines are then condensed, followed by a bromide to hydroxide ions exchange on an anion exchange resin.Phosphobetaines are then specifically formed by thermal elimination of ethanol above the critical micellar concentration.Howewer, when Hoffmann elimination competes with basic hydrolysis of the phenylphosphinic ester groups, acidic hydrolysis is preferred, followed by neutralization with an OH- anion exchange resin.This preparative specific synthesis procedure affords pure, neutral and inorganic salt free zwitterionic compounds for a whole series of homologues.The physical properties of such compounds are believed to be designed upon the chice of the substituents (alkyl chain length, interionic methylene number, ethoxy or phenyl substituent at the phosphorous atom).
- Germanaud, Laurent,Brunel, Sylvian,Chevalier, Yves,Le Perchec, Pierre
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p. 699 - 704
(2007/10/02)
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- Organophosphorus Chemistry. III. Synthesis of 3-Ethoxy-2-phenyl-1,3-azaphosphininane 3-Oxide
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Treatment of ethyl (3-bromopropyl)phosphonochloridate with benzylmagnesium chloride gave ethyl (benzyl)(3-bromopropyl)phosphinate.This underwent free-radical bromination to give ethyl (α-bromobenzyl)(3-bromopropyl)phosphinate.Cyclization with aqueous ammo
- Hewitt, David G.,Teese, Murray W.
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p. 205 - 210
(2007/10/02)
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