Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

Maestro, Aitor; Corte, Xabier del; López-Francés, Adrián; Marigorta, Eduardo Martı́nez de; Palácios, Francisco; Vicario, Javier

doi:10.3390/molecules26113202

Cited by 17 publications

(13 citation statements)

References 113 publications

(97 reference statements)

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“…However, the application of alafosfalin in medicine is limited due to its instability. It is shown that the correct design of the alkoxyl groups in the H -phosphite used for these compounds may significantly increase their antimicrobial properties ( Figure 1 ) [ 1 , 2 , 3 , 31 , 32 , 33 , 34 , 35 , 36 ].…”

Section: Introductionmentioning

confidence: 99%

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

et al. 2022

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We reported a new method dealing with the synthesis of novel pharmacologically relevant α-aminophosphonate derivatives via a lipase-catalyzed Kabachnik−Fields reaction with yields of up to 93%. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The developed protocol is applicable to a range of H-phosphites and organic amines, providing a wide substrate scope. A new class of α-aminophosphonate analogues possessing P-chiral centers was also synthesized. The synthesized compounds were characterized on the basis of their antimicrobial activities against E. coli. The impact of the various alkoxy groups on antimicrobial activity was demonstrated. The crucial role of the substituents, located at the aromatic rings in the phenylethyloxy and benzyloxy groups, on the inhibitory action against selected pathogenic E. coli strains was revealed. The observed results are especially important because of increasing resistance of bacteria to various drugs and antibiotics.

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Section: Introductionmentioning

confidence: 99%

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

et al. 2022

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“…The reaction also can be promoted by heating or microwave irradiation ( Kaboudin and Nazari, 2001 ; Ranu and Hajra, 2002 ; Macarie et al, 2019 ). In recent years, asymmetric synthesis of aminophosphonates has also been reported ( Maestro et al, 2018 , 2019 ; Maestro et al, 2020 ; Maestro et al, 2021 ).…”

Section: Synthetic Methods For the Preparation Of Hydroxy- And Amino-...mentioning

confidence: 99%

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

et al. 2022

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Phosphonates and bisphosphonates are stable analogs of phosphates and pyrophosphates that are characterized by one and two carbon–phosphorus bonds, respectively. Among the various phosphonates and bisphosphonates, hydroxy and amino substitutes are of interest as effective in medicinal and industrial chemistry. For example, hydroxy bisphosphonates have proven to be effective for the prevention of bone loss, especially in osteoporotic disease. On the other hand, different substitutions on the carbon atom connected to phosphorus have led to the synthesis of many different hydroxy- and amino-phosphonates and -bisphosphonates, each with its distinct physical, chemical, biological, therapeutic, and toxicological characteristics. Dialkyl or aryl esters of phosphonate and bisphosphonate compounds undergo the hydrolysis process readily and gave valuable materials with wide applications in pharmaceutical and agriculture. This review aims to demonstrate the ongoing preparation of various classes of hydroxy- and amino-phosphonates and -bisphosphonates. Furthermore, the current review summarizes and comprehensively describes articles on the biological applications of hydroxyl- and amino-phosphonates and -bisphosphonates from 2015 until today.

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“…The first can serve as surrogates for amino acids and reveal a broad spectrum of biological activity. [1][2][3][4][5][6][7][8][9][10] Phosphonamides, on the other hand, can be considered as analogues of the transition state of the hydrolysis of the peptide bond and are potent inhibitors of peptidases. 11 In addition, C,N-transfer of the phosphonyl group allows interconversions of aminophosphonates and phosphonamides.…”

Section: Introductionmentioning

confidence: 99%

Phosphonate-amidophosphate rearrangements in phosphorylated enamides and imines

Onys’ko¹,

Bezgubenko²,

Rassukana³

2022

Arkivoc

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Reactions of C,N-diphosphorylated dichlorovinyl amides with primary amines lead to the respective 2,2diaminovinylphosphonates. The latter undergo phosphoro-and prototropic rearrangements under heating to give diphosphorylated amidines. N-Sulfonyl iminophosphonates are converted into the corresponding Nphosphonyl iminophosphonates by reaction with diethyltrimethylsilylphosphite. The reaction of the latter with phosphonylimino trifluoropyruvate leads to the reduction of the C=N bond. Trimethylsilyl chloride mediated rearrangement of geminal amidobisphosphonates yields N-phosphonyl iminophosphonates.

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Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

Cited by 17 publications

References 113 publications

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Phosphonate-amidophosphate rearrangements in phosphorylated enamides and imines

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