409108-29-8Relevant articles and documents
Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
Kiviranta, Paeivi H.,Salo, Heikki S.,Leppaenen, Jukka,Rinne, Valtteri M.,Kyrylenko, Sergiy,Kuusisto, Erkki,Suuronen, Tiina,Salminen, Antero,Poso, Antti,Lahtela-Kakkonen, Maija,Wallen, Erik A.A.
, p. 8054 - 8062 (2008/12/23)
SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors.
Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide
Buijs, Wim,Comba, Peter,Corneli, Danny,Pritzkow, Hans
, p. 71 - 80 (2007/10/03)
N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L1)(TMAO)2] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L1)2-, coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L=1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction.
