- Optimization, continuation and lack of the one-step diphosphorylation reaction. Assay of modification of the tetraethyl-(pyrrolidine-2,2-diyl)bisphosphonate
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The optimization of the one-step diphosphorylation reaction is reported. The synthesis of new α-aminobisphosphonates with four- and six-membered rings and acyclic species with several substituents on the nitrogen atom and on the carbon atom bearing the two phosphorus atoms is described.
- Olive, Gilles,Jacques, Alain
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Read Online
- General and chemoselective bisphosphonylation of secondary and tertiary amides
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With Tf2O as the activation reagent, a mild and general method has been developed for the bisphosphonylation of both secondary and tertiary amides. The protocol is highly efficient and chemoselective, and it tolerates a number of sensitive functional groups such as cyano, ester, and aldehyde groups.
- Wang, Ai-E.,Chang, Zong,Sun, Wei-Ting,Huang, Pei-Qiang
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supporting information
p. 732 - 735
(2015/03/04)
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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 62; 63
(2014/09/03)
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- Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones
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A series of azetidin-2-ones substituted at positions 1, 3 and 4 of the azetidinone ring scaffold were synthesised and evaluated for antiproliferative, cytotoxic and tubulin-binding activity. In these compounds, the cis double bond of the vascular targeting agent combretastatin A-4 is replaced with the azetidinone ring in order to enhance the antiproliferative effects displayed by combretastatin A-4 and prevent the cis/trans isomerisation that is associated with inactivation of combretastatin A-4. The series of azetidinones was synthetically accessible via the Staudinger and Reformatsky reactions. Of a diverse range of heterocyclic derivatives, 3-(2-thienyl) analogue 28 and 3-(3-thienyl) analogue 29 displayed the highest potency in human MCF-7 breast cancer cells with IC50 values of 7 nM and 10 nM, respectively, comparable to combretastatin A-4. Compounds from this series also exhibited potent activity in MDA-MB-231 breast cancer cells and in the NCI60 cell line panel. No significant toxicity was observed in normal murine breast epithelial cells. The presence of larger, bulkier groups at the 3-position, for example, 3-naphthyl derivative 21 and 3-benzothienyl derivative 26, resulted in relatively lower antiproliferative activity in the micromolar range. Tubulin-binding studies of 28 (IC50 = 1.37 μM) confirmed that the molecular target of this series of compounds is tubulin. These novel 3-(thienyl) β-lactam antiproliferative agents are useful scaffolds for the development of tubulin-targeting drugs.
- O'Boyle, Niamh M.,Greene, Lisa M.,Bergin, Orla,Fichet, Jean-Baptiste,McCabe, Thomas,Lloyd, David G.,Zisterer, Daniela M.,Meegan, Mary J.
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experimental part
p. 2306 - 2325
(2011/05/12)
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- Synthesis of the new types of N-substituted aminomethylenebisorganophosphorus acids and their derivatives
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The interaction of esters of trivalent organophosphorus acids containing PH and POSiMe3 fragments with various derivatives of formamide is proposed as convenient methods for the synthesis of new N-substituted aminomethylenebisorganophos-phorus acids and their derivatives with three-, four-, and five-coordinated phosphorus. Also the new functionalized derivatives of the new aminomethylenebisphosphinic acids with substituted hydroxymethyl moieties are synthesized, and some properties of the obtained compounds are presented.
- Prishchenko, Andrey A.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.
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experimental part
p. 319 - 324
(2010/08/05)
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- NEW TYPES OF AMINOMETHYL ORGANOPHOSPHORUS COMPOUNDS
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We studied aminomethylation of various PH acids their derivatives containing highly reactive PH, PSi, POSi and PC(O) fragments: tris(trimethylsilyl)phosphine, trimethylsilyl esters of phosphorus(III) acids, pivaloylphosphonite, and hydrospirophosphoranes.Chloro-, alkoxy- or dialkylaminomethylamines, dialkylformamide acetals, azomethines, and enamines were used as aminomethylating reagents.Convenient methods for synthesizing previously unknown or difficult-to-obtain organic compounds of two-, three-, four, and five-coordinate phosphorus containing a P-C-N fragment were proposed.
- Prishchenko, A.A.,Livantsov, M.V.,Petrosyan, V.S.
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p. 1181 - 1193
(2007/10/02)
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- ZUR SYNTHESE VON BIS-ALKLYLMERCAPTO-METHANPHOSPHONSAEUREDIALKYLESTERN
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To find a simple and reproducible synthesis of bis-alkylmercaptomethane phosphonates 1 several methods had been examined.The reaction of chloro-dialkylmercaptomethanes 3 with trialkylphosphite (Method A) and the reaction of diethylmethanphosphonate 8 with mercaptanes (Method F) proved to be the best methods.
- Gross, Hans,Keitel, Iris,Costisella, Burkhard,Mikolajczyk, Marian,Midura, Wanda
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p. 257 - 262
(2007/10/02)
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