- The Facile Synthesis of O,O-Dialkyl 1-Aminoalkanephosphonates
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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
- Green, Donovan,Patel, Geeta,Elgendy, Said,Baban, Jehan A.,Claeson, Goeran,et al.
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- Synthesis and antimicrobial activity of phosphonopeptide derivatives incorporating single and dual inhibitors
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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.
- Anderson, Rosaleen J.,Gray, Mark,Marrs, Emma C. L.,Ng, Keng Tiong,Orenga, Sylvain,Perry, John D.
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- Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates
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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.
- Monbaliu, Jean-Christophe M.,Toupy, Thomas
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supporting information
p. 467 - 478
(2022/02/25)
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- Antimicrobial Compounds
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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.
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Paragraph 0186; 0187
(2017/08/26)
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- Surface-mediated solid phase reactions: A simple and new method for the synthesis of α-aminophosphonates under solvent-free conditions
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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.
- Kaboudin, Babak
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p. 880 - 881
(2007/10/03)
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- Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
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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
- Kaboudin, Babak,Nazari, Rahman
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p. 8211 - 8213
(2007/10/03)
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- 1-Aminoalkanephosphonates. Part II. A facile conversion of 1-aminoalkanephosphonic acids into O,O-diethyl 1-aminoalkanephosphonates
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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.
- Kudzin, Zbigniew H.,?yzwa, Piotr,?uczak, Jerzy,Andrijewski, Grzegorz
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- A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
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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.
- Demir, Ayhan S.,Tanyeli, Cihangir,Sesenoglu, Oezge,Demic, Serafettin,Evin, Oezden Oezel
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p. 407 - 410
(2007/10/02)
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- The facile synthesis of 1-aminophosphonates from 1-nitrophosphonate precursors
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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.
- Green, Donovan,Elgendy, Said,Patel, Geeta,Baban, Jehan A.,Skordalakes, Emmanuel,Husman, Wahid,Kakkar, Vijay V.,Deadman, John
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p. 303 - 306
(2007/10/03)
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- An efficient synthesis of diethyl 1-aminoalkylphosphonate hydrochlorides via the intermediate diethyl 1-azidoalkylphosphonates
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The title compounds 4 have been obtained in high yields in a one-step sequence by the Mitsunobu reaction of diethyl 1-hydroxyalkylphosphonates 1 with hydrazoic acid, and subsequence treatment of the intermediate azides 2 with triphenylphosphine, followed
- Gajda,Matusiak
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p. 2193 - 2203
(2007/10/02)
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- SYNTHESE DE PEPTIDES MODIFIES INCORPORANT UN MOTIF PHOSPHORE N OU C TERMINAL
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A general route to phosphopeptides with a 2-oxoalkylphosphonate moiety at the terminal N-amino group or with a 1-aminoalkylphosphonate moiety at the terminal C-carboxyl group is described.The method allows the preparation of various phosphopeptides with an α-alkylated carbon atom on the P-C bond from the very available dialkylpohosphonoalcanoic acids as starting products.
- Coutrot, Ph.,Grison, C.,Charbonnier-Gerardin, C.
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p. 9841 - 9868
(2007/10/02)
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- SYNTHESIS OF DERIVATIVES OF 1-AMINOETHYLPHOSPHONIC AND 1-AMINOETHYLPHOSPHINIC ACIDS AS SUBSTRATES FOR PENICILLINACYLASES
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Racemic and optically active N-phenylacetyl derivatives of 1-aminoethylphosphonic acid, 1-aminoethylphosphinic acid, and their mono- and diesters have been synthesized to study the substrate specificity of penicillinacylases.
- Solodenko, V. A.,Kasheva, T. N.,Mironenko, D. A.,Kozlova, E. V.,Shvyadas, V. K.,Kukhar, V. P.
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p. 1209 - 1215
(2007/10/02)
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- STUDIES ON ORGANOPHOSPHORUS COMPOUNDS. 65, A FACILE SYNTHETIC ROUTE TO PHOSPHONOPEPTIDES
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A direct procedure for the preparation of phosphonopeptides, containing either a N- or C-terminal phosphonic acid residue, is described.This method is based on a three component condensation reaction leading to diethyl 1-(N-carbobenzyloxyamino)-alkylphosp
- Yuan, Chengye,Wang, Guohong
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p. 207 - 212
(2007/10/02)
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- 1-Aminoalkanephosphonic acids. Addition of diethyl phosphite to N-diisobutylaluminio-aldimines
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A new route to 1-aminoalkanephosphonic acids starting from nitriles has been elaborated.The nitriles are reduced by Dibal-H into imine derivatives; addition with diethyl phosphite gives the corresponding 1-aminoalkanephosphonates.Hydrolysis of latter compounds gives the 1-aminoalkanephosphonic acids.
- Kudzin, Zbigniew H.,Majchrzak, Michal W.
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p. 245 - 248
(2007/10/02)
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- SYNTHESIS OF O,O-DIALKYL 1-AMINOALKANEPHOSPHONATE VIA N-PHOSPHINYLATED IMINES AND ENAMINES
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Synthesis of four O,O-diethyl 1-aminoalkanephosphonates (diethyl 1-aminoethanephosphonate 5a, diethyl 1-amino-1-phenylmethanephosphonate 5b, diethyl 1-amino-1-p-methoxyphenylmethanephosphonate 5c and diethyl 1-amino-2,2-dimethylpropanephosphonate 5d) star
- Krzyzanowska, Bozena,Pilichowska, Slawomira
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p. 165 - 177
(2007/10/02)
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- A Facile Conversion of Aminoalkanephosphonic Acids into Their Diethyl Esters. The Use of Unblocked Aminoalkanephosphonic Acids in Phosphono Peptide Synthesis
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A simple and efficient, two-step procedure for the preparation of diethyl aminoalkylphosphonates from aminoalkylphosphonic acids is reported.The obtained esters are useful as substrates in phosphono peptide synthesis.
- Kafarski, Pawel,Lejczak, Barbara
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p. 307 - 310
(2007/10/02)
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- CONVERSION OF AMINO ACIDS AND DIPEPTIDES INTO THEIR PHOSPHONIC ANALOGS; Aminoalkylphosphonic acids and peptides II.
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Acylamino carboxylic acids were degradated by the Hunsdiecker-reaction; the bromo-derivatives were reacted with NaPO(OC2H5)2.Aminophosphonic acids were obtained by acidic hydrolysis, and half-blocked derivatives by the selective removal of masking substituents.Two phosphonopeptides were also prepared by this route.
- Oesapay, George,Szilagyi, Ildiko,Seres, Jenoe
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p. 2977 - 2984
(2007/10/02)
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- STUDIES ON THE SYNTHESIS OF CHEMOTHERAPEUTICS. PART XIII. SYNTHESIS AND BIOLOGICAL STUDIES ON PHOSPHONOPEPTIDES HAVING ALKYL-, PHENYL-, AND HETEROCYCLIC SUBSTITUENTS.
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New antibacterial phosphonopeptides (3) were synthesized in order to improve the stability against hydrolysis by peptidase and the antibacterial spectra.Synthesis of them was accomplished by condensation of the N-carbobenzoxyamino acid with diethyl aminoalkylphosphonate followed by deprotection and hydrolysis.The antibacterial activity was evaluated in a defined medium and the stability against hydrolysis by rat liver homogenates was examined.Chemical modification of the N-terminal amino acid moiety of the phosphonopeptide containing sulfur or oxygen atom at β- or γ-position of the N-terminal α-amino acid residue lost rapidly their in vivo activity in spite of the high in vitro activity.The para substituted phenylalanyl-1-aminoethyl-phosphonic acids showed higher stability and slightly lower activity compared with those of the corresponding ortho- and meta-substituted isomers.Some of these para-substituted compounds (e.g. 9β, 10β, and 19β) exhibited the same level of the biological activity as that of Alafosfalin (1) in potency of the activity, broadness of the spectrum, and the serum level in mice after peroral administration.Phosphonopeptides consisted of unnatural amino acids and aminomethylphosphonic acid showed generally the extended spectra and activities, but these compounds were very fragile to hydrolysis by peptidase.None of phosphonopeptides containing 2-aminoethylphosphonic acid had the activity.
- Kametani, Tetsuji,Suzuki, Yukio,Kigasawa, Kazuo,Hiiragi, Mineharu,Wakisaka, Kikuo,et al.
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p. 295 - 319
(2007/10/02)
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- Synthesis of 1-Aminoalkane Phosphonic Acids via Benzhydrylic Schiff Bases
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A simple synthesis of 1-aminoalkanephosphonic acids is described.The addition of diethylphosphite to alkylidene- and arylidenebenzhydrylamines yields the N-benzhydryl-1-aminoalkanephosphonic acid esters.The title compounds are formed by treatment of the N-blocked esters with hydrobromic acid.The starting amine can be recycled from the hydrylbromide. - Key words: 1-Aminoalkane Phosphonic Acids, Benzhydrylic, Schiff Bases
- Issleib, Kurt,Doepfer, Klaus-Peter,Balszuweit, Arno
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p. 1392 - 1394
(2007/10/02)
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