107072-80-0Relevant academic research and scientific papers
Generation of a quenched phosphonate activity-based probe for labelling the active KLK7 protease
Bisyris, Evangelos,Kordopati, Golfo G.,Magriotis, Plato A.,Matsoukas, Minos,Pampalakis, Georgios,Sotiropoulou, Georgia,Zingkou, Eleni
, p. 6834 - 6841 (2021/08/20)
Kallikrein 7 (KLK7) is a chymotrypsin-like serine protease with established roles in skin diseases like the rare Netherton syndrome, an overdesquamating and inflammatory condition, but also common atopic dermatitis, and a potential drug target for these a
New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)
Viveros-Ceballos, José Luis,Matías-Valdez, Lizeth A.,Sayago, Francisco J.,Cativiela, Carlos,Ordó?ez, Mario
, p. 451 - 459 (2021/03/06)
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.
First Synthesis of (R)- and (S)-1,2,3,4-Tetrahydroisoquinoline-3-phosphonic Acid (TicP) Using a Pictet-Spengler Reaction
Viveros-Ceballos, José Luis,Ordó?ez, Mario,Sayago, Francisco J.,Jiménez, Ana I.,Cativiela, Carlos
, p. 2711 - 2719 (2016/06/08)
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
Comparative studies on the amidoalkylating properties of N-(1-methoxyalkyl)amides and 1-(N-acylamino)alkyltriphenylphosphonium salts in the michaelis-arbuzov-like reaction: A new one-pot transformation of N-(1-methoxyalkyl)amides into phosphonic or phosphinic analogs of N-Acyl-α-amino acids
Adamek, Jakub,Pazdzierniok-Holewa, Agnieszka,Zielinska, Katarzyna,Mazurkiewicz, Roman
, p. 967 - 980 (2013/08/23)
It was demonstrated that N-(1-methoxyalkyl)amides do not react with trimethyl phosphite under neutral or basic conditions. The treatment of N-(1-methoxyalkyl)amides with trialkyl phosphites or dialkyl phosphonites, triphenylphosphonium tetrafluoroborate, and Huenig's base caused immediate formation of the corresponding 1-(N-acylamino)-alkyltriphenylphosphonium tetrafluoroborates, followed by the slow Michaelis-Arbuzov-like reaction of phosphonium salt with phosphites or phosphonites to α-(N-acylamino)- alkanephosphonic or α-(N-acylamino)alkanephosphinic acid esters, respectively. A plausible mechanism of the considered transformations, assuming an equilibrium between N-(1-alkoxyalkyl)amide, triphenylphosphonium tetrafluoroborate, 1-(N-acylamino)alkyltriphenyl-phosphonium salt, N-acylimine, and N-acyliminium salts, is discussed.
