Synthesis of New Polyphosphonic Acids

Viornery, Carine; Péchy, Péter; Boegli, Mickael; Aronsson, Bjorn O.; Descouts, P.; Grätzel, Michaël

doi:10.1080/10426500210217

Cited by 19 publications

(3 citation statements)

References 23 publications

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“…( R , S )-2-Amino-4-(4-phosphono-butylsulfanyl)-butyric Acid (22). The reaction of diisopropyl-(4-bromo-butyl)-phosphonate ( 40 ; 0.3 g, 1 mmol) with d , l -homocysteine ( 5 ) according to method A afforded ( R , S )-2-amino-4-[4-(diisopropoxy-phosphoryl)-butylsulfanyl]-butyrate in the yield of 0.164 g (46%). 1 H NMR (DMSO): δ 1.227 (d, J = 6.2 Hz, 6H), 1.230 (d, J = 6.2 Hz, 6H), 1.54 (m, 2H), 1.59 (m, 2H), 1.67 (m, 2H), 2.01 (m, 2H), 2.51 (t, J = 7.0 Hz, 2H), 2.55 (ddd, J = 13.5, 9.1 and 6.0 Hz, 1H), 2.62 (ddd, J = 13.5, 9.2 and 6.5 Hz, 1H), 3.99 (bt, J ∼ 6 Hz, 1H), 4.53 (dh, 3 J (H, P) = 8.0, J (H, H) = 6.2 Hz, 1H), 4.54 (h, J = 6.2 Hz, 1H), 8.28 (b, 2H).…”

Section: Methodsmentioning

confidence: 99%

S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

et al. 2006

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A series of S-alkylated derivatives of homocysteine were synthesized and characterized as inhibitors of human recombinant betaine-homocysteine S-methyltransferase (BHMT). Some of these compounds inhibit BHMT with IC50 values in the nanomolar range. BHMT is very sensitive to the structure of substituents on the sulfur atom of homocysteine. The S-carboxybutyl and S-carboxypentyl derivatives make the most potent inhibitors, and an additional sulfur atom in the alkyl chain is well tolerated. The respective (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic, (R,S)-6-(3-amino-3-carboxy-propylsulfanyl)-hexanoic, and (R,S)-2-amino-4-(2-carboxymethylsulfanyl-ethylsulfanyl)-butyric acids are very potent inhibitors and are the strongest ever reported. We determined that (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid displays competitive inhibition with respect to betaine binding with a Kappi of 12 nM. Some of these compounds are currently being tested in mice to study the influence of BHMT on the metabolism of sulfur amino acids in vivo.

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Section: Methodsmentioning

confidence: 99%

S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

et al. 2006

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“…According to general procedures 220,221 for the Abruzov reaction, to a flame dried round bottom flask equipped with a reflux condenser connected to an inert atmosphere manifold, were added the appropriate reagents according to (Table 2.3). The flask was evacuated (2 min), backfilled with N 2 (g) and the reaction mixture refluxed for the appropriate time according to (Table 2.3) using an oil bath (175˚C).…”

Section: Abruzov Reactionmentioning

confidence: 99%

“…This compound was synthesized according to Method 5.2.2 by µW heating 1,3-dibromopropane (5.48 mL, 53.9 mmol, 1.1 eq.) and P(OiPr) 3 (11.16 221 See (Table 2.3, Entry xiii). This compound was synthesized according to Method 5.2.1 by refluxing 1,2-dibromoethane (40 mL, 394 mmol, 4.0 eq.)…”

Section: Abruzov Reactionmentioning

confidence: 99%

Detection and antimicrobial activity of immobilized quaternary ammonium antimicrobial monolayers on porous and non-porous surfaces

Porosa¹

2023

Preprint

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This research describes the development of novel, environmentally-friendly, non-releasing contact-active thin film coatings by immobilizing the quaternary ammonium (QA) antimicrobial group on a multitude of surfaces. Various chemical anchors based on organosilanes (i.e. textiles, silica, oxide surfaces), organosulfur comprising of thiol (noble metals), organophosphorus comprising of phosphonate and phosphonic acid (i.e. stainless steel (SS), titanium (Ti)), and catechol (Ti, SS) monolayers are employed to attach the QA antimicrobial onto metal surfaces, while benzophenone photoactive crosslinkers containing QA groups are used to coat plastic surfaces (C-H surfaces, i.e. polyethylene (PE), silicone (Si), polyvinylchloride (PVC)). Surfaces treated with covalently attached antimicrobial coatings function by killing microbes on contact, preventing surface attachment, colonization and contamination without releasing the chemical into the environment. The advantages of this method of delivery of the antimicrobial include a lower cost of application, decreased antimicrobial resistance, lower toxicity and increased environmental safety. Samples prepared by an overnight immersion in an ethanolic solution of phosphorus containing quats followed by an overnight cure at 100oC showed the highest antimicrobial reduction versus electrospray application and no curing. Short chain phosphonic acid quats and the organosilane quat were inactive on titanium. Antimicrobial activity of long chain phosphonate quats prepared by dip coating and annealing on metal surfaces (Ti, SS, Al) was tested by growth enumeration in the dry state utilizing methods developed in the Wolfaardt lab. All samples showed a 100% reduction (106 cells) of viable Salmonella, Arthrobacter, S.aureus and P.aeroguinosa after 2 hrs of contact time and maintained their activity over 24 hrs versus the uncoated controls. To demonstrate the phosphonate quats were truly immobilized, Ti samples from the first trial were washed in distilled H2O, dried, and re-innoculated with 106 Anthrobacter colonies. No visible colonies of Anthrobacter remained after 2 hrs of contact time with the Ti surfaces indicating a contact killing mechanism at play.

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Sodiated β‐Diphosphonate Carbanions: Characterization of the Tetrameric Cubane and the Hexameric Ladder Complexes [{(iPrO)₂P(O)}₂CHNa]₄ and [{(EtO)₂P(O)}₂CHNa]₆

2003

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Reaction of the methylene diphosphonates [(RO)2P(O)]2CH2, where R = iPr or Et, with the metalating reagents NaH, nBuNa or the superbasic mixture tBuONa/nBuLi leads to monodeprotonation, and formation of the complexes [{(iPrO)2P(O)}2CHNa]4 (1) and [{(EtO)2P(O)}2CHNa]6 (2). Single‐crystal X‐ray diffraction studies revealed that 1 is tetrameric in the solid state, with a central Na4O4 cubane core. Each metal in 1 is rendered pentacoordinate by binding to three μ3‐O phosphoryl bridges within the cubane, a chelating phosphoryl unit, and also a single iPrO group. In contrast, the structure of 2 is hexameric, and is composed of an unusual six‐rung Na6O6 ladder core. Three distinct sodium environments as well as μ1‐, μ2‐ and μ3‐O phosphoryl units are present within the ladder framework. No Na−C interactions are present in either 1 or 2. All of the six‐membered NaOPCPO chelate rings display localized P=O double bonds and partial multiple bonding on the P−C−P linkages (mean P−O: 1.49 Å, and mean P−C: 1.69 Å). Ab initio molecular orbital calculations (HF/6−31G*) on model complexes indicate that the hexameric arrangement found for 2 is thermodynamically more stable than the cubane structure of 1, in the absence of steric effects. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Synthesis of New Polyphosphonic Acids

Cited by 19 publications

References 23 publications

S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

Detection and antimicrobial activity of immobilized quaternary ammonium antimicrobial monolayers on porous and non-porous surfaces

Sodiated β‐Diphosphonate Carbanions: Characterization of the Tetrameric Cubane and the Hexameric Ladder Complexes [{(iPrO)₂P(O)}₂CHNa]₄ and [{(EtO)₂P(O)}₂CHNa]₆

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Synthesis of New Polyphosphonic Acids

Cited by 19 publications

References 23 publications

S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

S-Alkylated Homocysteine Derivatives: New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

Detection and antimicrobial activity of immobilized quaternary ammonium antimicrobial monolayers on porous and non-porous surfaces

Sodiated β‐Diphosphonate Carbanions: Characterization of the Tetrameric Cubane and the Hexameric Ladder Complexes [{(iPrO)2P(O)}2CHNa]4 and [{(EtO)2P(O)}2CHNa]6

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Sodiated β‐Diphosphonate Carbanions: Characterization of the Tetrameric Cubane and the Hexameric Ladder Complexes [{(iPrO)₂P(O)}₂CHNa]₄ and [{(EtO)₂P(O)}₂CHNa]₆