&amp;#969; -Phosphinyl-&amp;#945; -Amino Acids: Synthesis, and Development towards Use as Therapeutic Agents

Wardle, Nick J.; Bligh, S. W. Annie; Hudson, H. R.

doi:10.2174/138527207783221200

Cited by 27 publications

(1 citation statement)

References 75 publications

(117 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A few of these compounds have already been marketed. Various aspects of their biological activities in natural systems are reviewed [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. The biological effects of α-aminophosphonates are usually realized through enzyme inhibition.…”

Section: Introductionmentioning

confidence: 99%

Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study

Kocsis,

Varga,

Keshwan

et al. 2023

Pharmaceutics

View full text Add to dashboard Cite

α-Aminophosphonates are organophosphorus compounds with an obvious similarity with α-amino acids. Owing to their biological and pharmacological characteristics, they have attracted the attention of many medicinal chemists. α-Aminophosphonates are known to exhibit antiviral, antitumor, antimicrobial, antioxidant and antibacterial activities, which can all be important in pathological dermatological conditions. However, their ADMET properties are not well studied. The aim of the current study was to provide preliminary information about the skin penetration of three preselected α-aminophosphonates when applying them as topical cream formulations in static and dynamic diffusion chambers. The results indicate that aminophosphonate 1a, without any substituent in the para position, shows the best release from the formulation and the highest absorption through the excised skin. However, based on our previous study, the in vitro pharmacological potency was higher in the case of para-substituted molecules 1b and 1c. The particle size and rheological studies revealed that the 2% cream of aminophosphonate 1a was the most homogenous formulation. In conclusion, the most promising molecule was 1a, but further experiments are proposed to uncover the possible transporter interactions in the skin, optimize the topical formulations and improve PK/PD profiles in case of transdermal delivery.

show abstract

Section: Introductionmentioning

confidence: 99%

Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study

Kocsis,

Varga,

Keshwan

et al. 2023

Pharmaceutics

View full text Add to dashboard Cite

show abstract

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

View full text Add to dashboard Cite

Chiral amino acids featuring a phosphonate pendant arm are an important type of biologically active scaffold. Here in this review, we comprehensively summarize the modern synthetic methods towards asymmetric construction of chiral amino carboxylic‐phosphonic acid derivatives. The main streams of such interesting compounds include phosphono‐containing α‐, β‐, and γ‐amino acid derivatives, amino acid fluorophosphonate derivatives, amino acid cyclopropanylphosphonate derivatives, and bisphosphono‐amino acid derivatives. Chiral resolution protocols, chiral auxiliary‐directed syntheses, and valorization of the pool of abundant chiral amino acid resources remain contemporary concerns, and meanwhile catalytic enantioselective synthesis has also emerged as a potent strategy as demonstrated by the latest advances.magnified image

show abstract

Copper(II) Triflate Catalyzed Amination of 1,3‐Dicarbonyl Compounds

Ton

Himawan

Chang

et al. 2012

Chemistry A European J

View full text Add to dashboard Cite

A method to prepare α,α-acyl amino acid derivatives efficiently by Cu(OTf)(2)+1,10-phenanthroline (1,10-phen)-catalyzed amination of 1,3-dicarbonyl compounds with PhI=NSO(2) Ar is described. The mechanism is thought to initially involve aziridination of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, by the putative copper-nitrene/imido species generated from the reaction of the metal catalyst with the iminoiodane source. Subsequent ring opening of the resultant aziridinol adduct under the Lewis acidic conditions then provided the α-aminated product. The utility of this method was exemplified by the enantioselective synthesis of a precursor of 3-styryl-2-benzoyl-L-alanine.

show abstract

ω -Phosphinyl-α -Amino Acids: Synthesis, and Development towards Use as Therapeutic Agents

Cited by 27 publications

References 75 publications

Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study

Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Copper(II) Triflate Catalyzed Amination of 1,3‐Dicarbonyl Compounds

Contact Info

Product

Resources

About