17191-53-6Relevant academic research and scientific papers
Synthesis of the marine natural product barbamide
Nguyen,Willis,Gerwick
, p. 1934 - 1935 (2007/10/03)
The first total synthesis of the trichlorinated natural product barbamide is described. The convergent approach involves coupling (S)-3-trichloromethylbutanoyl chloride with Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) to give 15 followed by additi
Chiral ligands containing heteroatoms; 9. General procedures for the synthesis of optically active 1-(2-pyridyl)alkylamines from α-amino acids
Falorni,Chelucci,Conti,Giacomelli
, p. 972 - 976 (2007/10/02)
General syntheses of 1-(2-pyridyl)alkylamines and N-methyl or N,N-dimethyl-1-(2-pyridyl)alkylamines from optically active α-amino acids are described. The presented procedures are based on catalyzed co-cyclotrimerization of the suitable nitriles with acet
Development of Potent and Selective CCK-A Receptor Agonists from Boc-CCK-4: Tetrapeptides Containing Lys(Nε)-Amide Residues
Shiosaki, Kazumi,Lin, Chun Wel,Kopecka, Hana,Craig, Richard A.,Bianchi, Bruce R.,et al.
, p. 2007 - 2014 (2007/10/02)
A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(Nε-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-A receptor agonists.These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al.J.Med.Chem. 1991,34,2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series.A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives.Sulfation of phenolic amides appended onto the ε-amino group of the lysine did not affect affinity for the CCK-A receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor.The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis.Both effects were blocked by selective CCK-A receptor antagonists
