65164-84-3

Upstream product

• 101-02-0 triphenyl phosphite 
• 621-84-1 O-benzyl carbamate 
• 100-52-7 benzaldehyde 
• 372199-85-4 [phenyl-(toluene-4-sulfonyl)-methyl]-carbamic acid benzyl ester 

Downstream Products

• 472966-69-1 ((S)-Benzyloxycarbonylamino-phenyl-methyl)-phosphonic acid monophenyl ester 
• 472966-68-0 ((R)-Benzyloxycarbonylamino-phenyl-methyl)-phosphonic acid monophenyl ester 
• 901773-70-4 (formylamino-phenyl-methyl)-phosphonic acid diphenyl ester 
• 1403781-79-2 diphenyl (isothiocyanato(phenyl)methyl)phosphonate 
• 163017-99-0 4-(2-Diphenylacetylamino-2-phenyl-ethyl)-benzoic acid methyl ester 
• 254982-95-1 (isocyanato-phenyl-methyl)-phosphonic acid diphenyl ester 
• 472966-61-3 methyl N-[[{[(benzyloxy)carbonyl]amino}(phenyl)methyl](phenoxy)phosphoryl]-L-valinate 
• 472966-70-4 (R)-(-)-N-benzyl O-phenyl-P-[{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonamidate 
• 472966-71-5 C₂₈H₂₇N₂O₄P 
• 472966-59-9 O-phenyl N-benzyl-P-[{[(benzyloxy)carbonyl]amino}(phenyl)methyl]phosphonamidate 

Relevant academic research and scientific papers

One-pot synthesis of α-aminophosphonates by yttrium-catalyzed Birum-Oleksyszyn reaction

For the first time, yttrium triflate was used as an efficient green catalyst for the synthesis of α-aminophosphonates through a one-pot three-component Birum-Oleksyszyn reaction. Under the action of this Lewis acid, enhancement of the yield and reaction c

A Suite of Activity-Based Probes to Dissect the KLK Activome in Drug-Resistant Prostate Cancer

Kallikrein-related peptidases (KLKs) are a family of secreted serine proteases, which form a network (the KLK activome) with an important role in proteolysis and signaling. In prostate cancer (PCa), increased KLK activity promotes tumor growth and metastasis through multiple biochemical pathways, and specific quantification and tracking of changes in the KLK activome could contribute to validation of KLKs as potential drug targets. Herein we report a technology platform based on novel activity-based probes (ABPs) and inhibitors enabling simultaneous orthogonal analysis of KLK2, KLK3, and KLK14 activity in hormone-responsive PCa cell lines and tumor homogenates. Importantly, we identifed a significant decoupling of KLK activity and abundance and suggest that KLK proteolysis should be considered as an additional parameter, along with the PSA blood test, for accurate PCa diagnosis and monitoring. Using selective inhibitors and multiplexed fluorescent activity-based protein profiling (ABPP), we dissect the KLK activome in PCa cells and show that increased KLK14 activity leads to a migratory phenotype. Furthermore, using biotinylated ABPs, we show that active KLK molecules are secreted into the bone microenvironment by PCa cells following stimulation by osteoblasts suggesting KLK-mediated signaling mechanisms could contribute to PCa metastasis to bone. Together our findings show that ABPP is a powerful approach to dissect dysregulation of the KLK activome as a promising and previously underappreciated therapeutic target in advanced PCa.

A novel theranostic activity-based probe targeting kallikrein 7 for the diagnosis and treatment of skin diseases

We applied a newin silicoapproach for using protease-substrate motifs to design a kallikrein 7 (KLK7)-specific phosphonate activity-based probe (ABP) to quantify the active KLK7in situ. Epidermal application of the ABP-inhibitor onSpink5?/?Klk5

NOVEL AMINOALKYLPHOSPHONATE COMPOUNDS AND METHODS USING SAME

The present invention includes aminoalkylphosphonate compounds that are useful in preventing and/or treating prostate cancer in a male subject. The present invention further includes methods of preventing and/or treating prostate cancer in a male subject

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

The synthesis of a library of structurally variable aromatic esters of (benzyloxycarbonylamino)(aryl)methylphosphonic acids is described by means of the Oleksyszyn reaction. The library was enlarged by the application of a Suzuki-Miayra approach and by preparation of mixed esters.

Convenient syntheses of novel 1-isothiocyano-alkylphosphonate diphenyl ester derivatives with potential biological activity

Herein, we describe a convenient method for the syntheses of novel 1-isothiocyano-alkylphosphonate diaryl ester derivatives and their antiproliferative activity. The syntheses are based on dithiocarbamates obtained in situ with the use of carbon disulfide

New aromatic monoesters of α-aminoaralkylphosphonic acids as inhibitors of aminopeptidase N/CD13

A series of new aromatic monoesters of α-aminoaralkylphosphonic acids were synthesized by selective hydrolysis of corresponding aromatic diesters of α-aminoaralkylphosphonic acids. New potential inhibitors of aminopeptidase N/CD13, an enzyme important in tumour angiogenesis, were developed. Some derivatives of the homophenylalanine and norleucine related monoaryl phosphonates displayed higher inhibition potency than corresponding α-aminoaralkylphosphonic acids toward aminopeptidase N/CD13. The effect of one of the new inhibitors on the growth of human PANC-1 and HT-1080 cell lines was examined, either alone or in combination with TNF-α.

A simple and efficient access to α-amino phosphonates from N-benzyloxycarbonylamino sulfones using indium(III) chloride

(Chemical Equation Presented) Treatment of N-benzyloxycarbonylamino sulfones with triethyl phosphite catalyzed by InCl3 produces the corresponding protected α-amino phosphonates in high yields (71-92%).

Synthesis of phosphonodipeptide conjugates of ursolic acid and their homologs

To prepare novel derivatives of naturally bioactive 3β-hydroxy-urs-12- en-28-oic acid (ursolic acid) with unusual properties and broad spectrum of activities, a number of chemical reactions were conducted. First, a variety of a-aminophosphonates were prepared by a series of reactions involving the three-component Mannich type reaction as a key step. Second, an array of phosphonodipeptides and their homologs was synthesized through multistep reactions including condensation of phthalic anhydride with glycine or β-alanine, chlorination of N-blocked amino acids, coupling of acid chloride with α-aminophosphonates and sequential hydrazinolysis. Finally, new classes of phosphonodipeptide conjugates of ursolic acid and their homologs were obtained by condensation of 3β-acetoxy-urs-12-en-28-oyl chloride with phosphonodipeptides and their homologs.

New potent cathepsin G phosphonate inhibitors

Cathepsin G is an enzyme with dual chymotrypsin and trypsin-like specificity. As a leukocyte proteinase it is involved in the early stages of the immune response. In this work the synthesis and inhibitory activity of diaryl phosphonic-type irreversible ca