54788-35-1Relevant academic research and scientific papers
The Facile Synthesis of O,O-Dialkyl 1-Aminoalkanephosphonates
Green, Donovan,Patel, Geeta,Elgendy, Said,Baban, Jehan A.,Claeson, Goeran,et al.
, p. 6917 - 6920 (1993)
O,O-Dialkyl 1-hydroxyiminoalkanephosphonates 1, may be conveniently reduced to O,O-dialkyl 1-aminoalkanephosphonates 2, at ambient temperature by application of lithium borohydride/trimethylsilyl chloride
Synthesis and antimicrobial activity of phosphonopeptide derivatives incorporating single and dual inhibitors
Anderson, Rosaleen J.,Gray, Mark,Marrs, Emma C. L.,Ng, Keng Tiong,Orenga, Sylvain,Perry, John D.
, (2020)
In diagnostic microbiology, culture media are widely used for detection of pathogenic bacteria. Such media employ various ingredients to optimize detection of specific pathogens such as chromogenic enzyme substrates and selective inhibitors to reduce the presence of commensal bacteria. Despite this, it is rarely possible to inhibit the growth of all commensal bacteria, and thus pathogens can be overgrown and remain undetected. One approach to attempt to remedy this is the use of “suicide substrates” that can target specific bacterial enzymes and selectively inhibit unwanted bacterial species. With the purpose of identifying novel selective inhibitors, six novel phosphonopeptide derivatives based on D/L-fosfalin and β-chloro-L-alanine were synthesized and tested on 19 different strains of clinically relevant bacteria. Several compounds show potential as useful selective agents that could be exploited in the recovery of several bacterial pathogens including Salmonella, Pseudomonas aeruginosa, and Listeria.
Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates
Monbaliu, Jean-Christophe M.,Toupy, Thomas
supporting information, p. 467 - 478 (2022/02/25)
Herein is described the development of an intensified continuous flow process for the preparation of a library of alkyl phosphonates through a Michaelis-Arbuzov rearrangement. A careful process optimization and thorough analysis of the competitive reactions led to a very attractive protocol with unprecedented productivities (up to 4.97 kg of material per day) and a low environmental footprint with the absence of solvent, additives, catalysts, and waste. In-line low-field 31P NMR monitoring was conveniently implemented for rapid optimization and process monitoring. Two key alkyl phosphonate intermediates were also assessed for the unprecedented diazene dicarboxylate-mediated electrophilic amination under continuous flow conditions toward the α-aminophosphonic acid derivatives of Pphenylalanine and Palanine, bioisosters of the natural amino acids phenylalanine and alanine, respectively.
Antimicrobial Compounds
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Paragraph 0186; 0187, (2017/08/26)
An antimicrobial compound, as well as the salts, derivatives and analogues thereof, said compound being represented by the general formula (I): wherein R1 represents a peptide part P1 or a peptide part P2.
Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
Kaboudin, Babak,Nazari, Rahman
, p. 8211 - 8213 (2007/10/03)
A simple, efficient and general method has been developed for the synthesis of 1-aminoalkyl phosphonates through a one-pot reaction of aldehydes with amines in the presence of acidic alumina under solvent-free conditions using microwave irradiation. It wa
Surface-mediated solid phase reactions: A simple and new method for the synthesis of α-aminophosphonates under solvent-free conditions
Kaboudin, Babak
, p. 880 - 881 (2007/10/03)
Alumina-supported ammonium formate was found to be an efficient reagent for the synthesis of 1-aminophosphonates from aldehydes and diethyl phosphite. This method is an easy, rapid and high-yielding reaction for the synthesis of 1-aminophosphonates.
1-Aminoalkanephosphonates. Part II. A facile conversion of 1-aminoalkanephosphonic acids into O,O-diethyl 1-aminoalkanephosphonates
Kudzin, Zbigniew H.,?yzwa, Piotr,?uczak, Jerzy,Andrijewski, Grzegorz
, p. 44 - 46 (2007/10/03)
1-(N-Trifluoroacetylamino)alkanephosphonate O,O-diethyl esters 2C, obtained from parent 1-aminoalkanephosphonic acids 1, have been selectively deprotected on the amino function affording O,O-diethyl 1-aminoalkanephosphonates 3. Protonation constants of all amino esters 3 synthesized have been determined by potentiometric titration.
The facile synthesis of 1-aminophosphonates from 1-nitrophosphonate precursors
Green, Donovan,Elgendy, Said,Patel, Geeta,Baban, Jehan A.,Skordalakes, Emmanuel,Husman, Wahid,Kakkar, Vijay V.,Deadman, John
, p. 303 - 306 (2007/10/03)
1-Aminophosphonates may be generated in high yield and spectroscopic purity by the treatment of 1-nitrophosphonates with LiBH4/Me3SiCl in THF at room temperature.
A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
Demir, Ayhan S.,Tanyeli, Cihangir,Sesenoglu, Oezge,Demic, Serafettin,Evin, Oezden Oezel
, p. 407 - 410 (2007/10/02)
A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.
