425704-52-5Relevant articles and documents
Synthesis and inhibitory studies of phosphonic acid analogues of homophenylalanine and phenylalanine towards alanyl aminopeptidases
Wanat, Weronika,Talma, Micha?,Dziuk, B?a?ej,Kafarski, Pawe?
, p. 1 - 22 (2020/09/18)
A library of novel phosphonic acid analogues of homophenylalanine and phenylalanine, containing fluorine and bromine atoms in the phenyl ring, have been synthesized. Their inhibitory properties against two important alanine aminopeptidases, of human (hAPN, CD13) and porcine (pAPN) origin, were evaluated. Enzymatic studies and comparison with literature data indicated the higher inhibitory potential of the homophenylalanine over phenylalanine derivatives towards both enzymes. Their inhibition constants were in the submicromolar range for hAPN and the micromolar range for pAPN, with 1-amino-3-(3-fluorophenyl) propylphosphonic acid (compound 15c) being one of the best low-molecular inhibitors of both enzymes. To the best of our knowledge, P1 homophenylalanine analogues are the most active inhibitors of the APN among phosphonic and phosphinic derivatives described in the literature. Therefore, they constitute interesting building blocks for the further design of chemically more complex inhibitors. Based on molecular modeling simulations and SAR (structure-activity relationship) analysis, the optimal architecture of enzyme-inhibitor complexes for hAPN and pAPN were determined.
Catalytic asymmetric cross-dehydrogenative coupling: Activation of C-H bonds by a cooperative bimetallic catalyst system
Cao, Weidi,Liu, Xiaohua,Peng, Ruixue,He, Peng,Lin, Lili,Feng, Xiaoming
supporting information, p. 3470 - 3472 (2013/05/23)
A cooperative bimetallic catalyst system was applied in the catalytic asymmetric cross-dehydrogenative coupling of β-ketoesters and xanthene. Various optically active xanthene derivatives bearing a quaternary stereogenic carbon center were obtained in moderate to good yields (up to 90%) with excellent enantioselectivities (up to 99% ee). Meanwhile, a transition-state model was proposed to explain the origin of the asymmetric induction.
Nickel-catalyzed reductive hydroesterification of styrenes using CO 2 and MeOH
Gonzalez-Sebastian, Lucero,Flores-Alamo, Marcos,Garcia, Juventino J.
, p. 8200 - 8207 (2013/02/22)
Complexes [(dippe)Ni(μ-H)]2 (A) (dippe = 1,2-bis-di- isopropylphosphino)ethane) and [(dtbpe)Ni(μ-H)]2 (B) (dtbpe = 1,2-bis-di-tert-butylphospino)ethane) catalyze the reductive hydroesterification of styrenes with the use of CO2 and MeOH. The latter acts as a hydrogen source and as an esterificating agent, to yield the corresponding branched and linear esters in moderate to good yields. In all of the studied reactions the linear esters were obtained in higher amounts than the branched ones. When the hydroesterification reaction was carried out using a stoichiometric metal/substrate ratio, the complexes [(P-P)Ni(CO)2] and [(P-P)Ni(CO3)] (P-P = dippe or dtbpe) were isolated and characterized by standard spectroscopic methods. Compounds [(dtbpe)Ni(CO) 2] and [(dtbpe)Ni(CO3)] were also fully characterized by single-crystal X-ray diffraction.