77526-73-9

Upstream product

• 140-29-4 phenylacetonitrile 
• 762-04-9 phosphonic acid diethyl ester 
• 80993-28-8 [1-(Benzhydryl-amino)-2-phenyl-ethyl]-phosphonic acid diethyl ester 
• 77526-86-4 {1-[(E)-Hydroxyimino]-2-phenyl-ethyl}-phosphonic acid diethyl ester 
• 103-82-2 phenylacetic acid 
• 103-80-0 phenylacetyl chloride 
• 67257-48-1 (2-Phenyl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-ethyl)-phosphonic acid diethyl ester 
• 107072-80-0 diethyl 1?(N?benzyloxycarbonylamino)?2?phenylethylphosphonate 
• 108-88-3 toluene 
• 100-39-0 benzyl bromide 
• 141920-88-9 (1-Azido-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 124810-56-6 diethyl 1-hydroxy-2-phenylethylphosphonate 
• 80993-22-2 benzylmethylidenediphenylmethylamine 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 72397-75-2 α-Amino-β-phenylethylphosphorsaeure-monoethylester 
• 146036-90-0 <1-(tert-Butyloxycarbonyl-L-alanyl-amino)-2-phenyl>ethylphosphonate de diethyle 
• 123213-83-2 C₅₅H₇₂N₅O₁₀P 
• 6324-00-1 1-amino-2-phenylethanephosphonic acid 
• 66609-42-5 D-Phenylalanine phosphonate 
• 36992-14-0 L-Phenylalanine phosphonate 
• 108327-51-1 diethyl (1-amino-2-cyclohexylethyl)phosphonate 
• 95852-63-4 3-Benzyloxycarbonylamino-N-[1-(diethoxy-phosphoryl)-2-phenyl-ethyl]-succinamic acid benzyl ester 
• 137619-55-7 (1-Amino-2-cyclohexyl-ethyl)-phosphonic acid 

Relevant academic research and scientific papers

New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)

Two new strategies for the efficient synthesis of racemic 1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid (TicP) (±)-2 have been developed. The first strategy involves the electron-transfer reduction of the easily obtained α,β-dehydro phosphonophenylalanine followed by a Pictet–Spengler cyclization. The second strategy involves a radical decarboxylation–phosphorylation reaction on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic). In both strategies, the highly electrophilic N-acyliminium ion is formed as a key intermediate, and the target compound is obtained in good yield using mild reaction conditions and readily available starting materials, complementing existing methodologies and contributing to the easy accessibility of (±)-2 for further research.

Phosphonic acid analogs of fluorophenylalanines as inhibitors of human and porcine aminopeptidases N: Validation of the importance of the substitution of the aromatic ring

A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.

Pharmacophore Mapping of Thienopyrimidine-Based Monophosphonate (ThP-MP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase

The human farnesyl pyrophosphate synthase (hFPPS), a key regulatory enzyme in the mevalonate pathway, catalyzes the biosynthesis of the C-15 isoprenoid farnesyl pyrophosphate (FPP). FPP plays a crucial role in the post-translational prenylation of small GTPases that perform a plethora of cellular functions. Although hFPPS is a well-established therapeutic target for lytic bone diseases, the currently available bisphosphonate drugs exhibit poor cellular uptake and distribution into nonskeletal tissues. Recent drug discovery efforts have focused primarily on allosteric inhibition of hFPPS and the discovery of non-bisphosphonate drugs for potentially treating nonskeletal diseases. Hit-to-lead optimization of a new series of thienopyrimidine-based monosphosphonates (ThP-MPs) led to the identification of analogs with nanomolar potency in inhibiting hFPPS. Their interactions with the allosteric pocket of the enzyme were characterized by crystallography, and the results provide further insight into the pharmacophore requirements for allosteric inhibition.

First Synthesis of (R)- and (S)-1,2,3,4-Tetrahydroisoquinoline-3-phosphonic Acid (TicP) Using a Pictet-Spengler Reaction

We report here a practical and efficient synthesis of diethyl 1,2,3,4-tetrahydroisoquinoline-3-phosphonate derivatives. The target compounds were prepared in good yield using a Pictet-Spengler reaction involving α-amino phosphonates that were easily obtai

MONOMETHYLVALINE COMPOUNDS HAVING PHENYLALANINE CARBOXY MODIFICATIONS AT THE C-TERMINUS

Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) having a carboxylic acid equivalent at the C-terminal phenylalanine were prepared and attached to ligands through various linkers, including maleimidocaproyl-val-cit-PAB. The resulting ligand drug conjugates were active in vitro and in vivo.

Sulfonamide derivative as a matrix metalloproteinase inhibitor

The present invention provides a novel sulfonamide derivative of general formula (I) useful as an inhibitor of matrix metalloproteinase (MMP), its isomers, pharmaceutically acceptable salts thereof and a process for preparing the same. Since the sulfonami

1-Aminoalkanephosphonates. Part II. A facile conversion of 1-aminoalkanephosphonic acids into O,O-diethyl 1-aminoalkanephosphonates

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.

A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

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.

An efficient synthesis of diethyl 1-aminoalkylphosphonate hydrochlorides via the intermediate diethyl 1-azidoalkylphosphonates

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

SYNTHESE DE PEPTIDES MODIFIES INCORPORANT UN MOTIF PHOSPHORE N OU C TERMINAL

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.