105382-09-0Relevant articles and documents
A new and practical synthesis of α-amino acids from alkenyl boronic acids
Petasis,Zavialov
, p. 445 - 446 (1997)
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New anthranilic acid based antagonists with high affinity and selectivity for the human cholecystokinin receptor 1 (hCCK1-R)
Pavan, Michela V.,Lassiani, Lucia,Berti, Federico,Stefancich, Giorgio,Ciogli, Alessia,Gasparrini, Francesco,Mennuni, Laura,Ferrari, Flora,Escrieut, Chantal,Marco, Esther,Makovec, Francesco,Fourmy, Daniel,Varnavas, Antonio
experimental part, p. 5769 - 5785 (2011/10/09)
The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.
Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel-Crafts reaction with trifluoromethanesulfonic acid
Murashige, Ryo,Hayashi, Yuka,Hashimoto, Makoto
supporting information; scheme or table, p. 6566 - 6568 (2009/04/05)
An efficient Friedel-Crafts reaction of TFA-Asp(Cl)-OMe and stoichiometric amounts of benzene was established by using neat trifluoromethanesulfonic acid (TfOH) as solvent and catalyst under a mild condition. This methodology has been applied to many arom