- Selective esterification of phosphonic acids
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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.
- Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
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- SMALL MOLECULE AUTOPHAGY INDUCERS FOR THE TREATMENT OF CANCER AND NEURODEGENERATIVE DISEASES
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Disclosed herein are compounds and methods for treating cancer and neurodegenerative diseases. In some examples, the compounds increase autophagy.
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Page/Page column 41; 42
(2020/11/03)
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- Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation
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The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.
- Ma, Xiantao,Xu, Qing,Li, Huan,Su, Chenliang,Yu, Lei,Zhang, Xu,Cao, Hongen,Han, Li-Biao
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supporting information
p. 3408 - 3413
(2018/08/06)
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- Synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds
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The invention discloses a synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds. According to the synthetic method, alcohols which are cheap, easy to get, wide in source, stable and low in toxicity serve as alkylating reagents, iodine salt which is cheap and easy to get serves as catalysts, no solvent is needed, and the alkyl group phosphorous acid diester compounds can be selectively directly obtained after a reaction. The reaction method is simple, the condition is mild, no organic solvent is needed and operation is simple. According to the method, the requirements for reaction conditions are low, various types of alcohols such as a benzyl group type, an allyl type and a fat type can be utilized as the alkylate reagents to implement the synthesis of different types of substituted alkyl group phosphorous acid diester, and the method can be further expanded to the synthesis of the alkyl group phosphinic acid ester compounds through the reaction between the substituted phosphonous acid diester and the alcohols.
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Paragraph 0054; 0055; 0056; 0057
(2017/04/26)
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- Efficient synthesis of small-sized phosphonated dendrons: Potential organic coatings of iron oxide nanoparticles
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We report herein the synthesis of biocompatible small-sized phosphonated monomers and dendrons used as functional coatings of metal oxide nanoparticles, more specifically superparamagnetic iron oxides (SPIOs) for magnetic resonance imaging (MRI) and therapy through hyperthermia. The molecules were engineered to modulate their size, their hydrophilic and/or biocompatible character (poly(amido)amine versus oligoethyleneglycol), the number of anchoring phosphonate groups (monophosphonate versus phosphonic tweezers) and the number of peripheral functional groups for further grafting of dyes or specific vectors. Such a library of hydrophilic phosphonic acids opens new possibilities for the investigation of dendronized nanohybrids as theranostics.
- Garofalo, Antonio,Parat, Audrey,Bordeianu, Catalina,Ghobril, Cynthia,Kueny-Stotz, Marie,Walter, Aurlie,Jouhannaud, Julien,Begin-Colin, Sylvie,Felder-Flesch, Delphine
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p. 5226 - 5239
(2014/12/10)
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- Novel Phosphinic Acid-Containing Thyromimetics
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The present invention relates to compounds of phosphonic acid-containing T3 mimetics and monoesters thereof, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndrome x and diabetes.
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Page/Page column 99
(2009/02/11)
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- Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs
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Phosphonic acid (PA) thyroid hormone receptor (TR) agonists were synthesized to exploit the poor distribution of PA-based drugs to extrahepatic tissues and thereby to improve the therapeutic index. Nine PAs showed excellent TR binding affinities (TRβ
- Boyer, Serge H.,Jiang, Hongjian,Jacintho, Jason D.,Reddy, Mali Venkat,Li, Haiqing,Li, Wenyu,Godwin, Jennifer L.,Schulz, William G.,Cable, Edward E.,Hou, Jinzhao,Wu, Rongrong,Fujitaki, James M.,Hecker, Scott J.,Erion, Mark D.
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experimental part
p. 7075 - 7093
(2009/11/30)
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- NOVEL PHOSPHORUS-CONTAINING THYROMIMETICS
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The present invention relates to compounds of phosphonic acid containing T3 mimetics, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndromex and diabetes.
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- Negative inotropic activity of para-substituted diethyl benzylphosphonates related to fostedil
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Several para-substituted diethyl benzylphosphonates related to the calcium antagonist diethyl 4-(2-benzothiazolyl)benzylphosphonate (fostedil) have been studied.They produce a dose-dependent negative inotropic effect on left atrial muscle isolated from guinea pig heart.Some of the compounds are equipotent or slightly more potent than fostedil and diltiazem taken as reference drugs.Structure-activity relationships are discussed.Keywords: calcium antagonists / p-substituted diethyl benzylphosphonates / cardiodepressant activity
- Bellucci, Christina,Gualtieri, Fulvio,Chiarini, Alberto
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p. 473 - 478
(2007/10/02)
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- Immonium salts and derivatives thereof
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There are provided: novel aryloxy immonium salts, prepared by the reaction of their corresponding haloformates with amides; and phenolic compositions corresponding to the aryloxy immonium salts. These novel aryloxy immonium salts and their corresponding phenolic compositions have utility as chemical intermediates, antioxidants, stabilizers and antibacterials.
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- Immonium salts and derivatives thereof
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There are provided: novel aryloxy immonium salts, prepared by the reaction of their corresponding haloformates with amides; and phenolic compositions corresponding to the aryloxy immonium salts. These novel aryloxy immonium salts and their corresponding phenolic compositions have utility as chemical intermediates, antioxidants, stabilizers and antibacterials.
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