73913-65-2Relevant academic research and scientific papers
Enantioselective synthesis of α-secondary and α-tertiary piperazin-2- Ones and piperazines by catalytic asymmetric allylic alkylation
Korch, Katerina M.,Eidamshaus, Christian,Behenna, Douglas C.,Stoltz, Brian M.,Nam, Sangkil,Horne, David
supporting information, p. 179 - 183 (2015/02/05)
The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2- ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to that of their corresponding imatinib counterparts.
Synthesis, crystal structure and insecticidal activity of the optical active neonicotinoid analogues
Xue, Sijia,Bu, Hongfei,Liu, Li,Xu, Xiao,Ma, Xubo
scheme or table, p. 1011 - 1016 (2012/01/06)
Eight novel neonicotinoid analogues 1-(2-tetrahydrofurfuryl)-5-substituted- 1,3,5-hexahydrotriazine-2-N-nitroimines 3a - 3h were synthesized, and their structures were characterized by 1H NMR, IR and elemental analysis. The stereostructure of 3a was determined by the single-crystal X-ray analysis, which exhibits a half-chair conformation and dihedral angle is 49.70° . The preliminary bioassay tests showed that all the title compounds exhibited good insecticide activities against Nilaparvata legen (N. legen).
Anthranilic acid based CCK1 receptor antagonists: Blocking the receptor with the same 'words' of the endogenous ligand
Lassiani, Lucia,Pavan, Michela V.,Berti, Federico,Kokotos, George,Markidis, Theodoros,Mennuni, Laura,Makovec, Francesco,Varnavas, Antonio
experimental part, p. 2336 - 2350 (2009/09/05)
The anthranilic acid diamides represent the more recent class of nonpeptide CCK1 receptor antagonists. This class is characterized by the presence of anthranilic acid, used as a molecular scaffold, and two pharmacophores selected from the C-terminal tetrapeptide of CCK. The lead compound coded VL-0395, endowed with sub-micromolar affinity towards CCK1 receptors, was characterized by the presence of Phe and 2-indole moiety at the C- and N-termini of anthranilic acid, respectively. Herein we describe the first step of the anthranilic acid C-terminal optimization using, instead of Phe, aminoacids belonging to the primary structure of CCK-8 and other not coded residues. Thus we demonstrate that the CCK1 receptor affinity depends on the nature of the aminoacidic side chain as well as that the free carboxy group of the alpha-aminoacids is crucial for the binding. The R enantiomers of the most active compounds represent the eutomers of this class of antagonists confirming thus the stereo preference of the receptor. Moreover this SAR study demonstrates that the receptor binding pocket, that host the aminoacidic side chain, results much more tolerant respect to that accommodating the indole ring. As a result, an appropriate variation of the aminoacidic side chain could provide a better CCK1 receptor affinity diorthosis.
Diastereoselective reductive amination of aryl trifluoromethyl ketones and α-amino esters
Hughes, Greg,Devine, Paul N.,Naber, John R.,O'Shea, Paul D.,Foster, Bruce S.,McKay, Daniel J.,Volante
, p. 1839 - 1842 (2008/02/12)
(Chemical Equation Presented) Reductionist art: Careful choice of the reducing agent in the reductive amination of trifluoromethyl ketones with α-amino esters allows stereoselective access, from the imine formed, to either the R,S or S,S diastereomers of the resulting amino acids. Whereas NaBH4 affords the R,S diastereomers, Zn(BH4)2 affords the S,S diastereomers (see scheme), which can be easily converted into potent cathepsin K inhibitors.
CLEAVAGE OF THE N-PChd GROUP FROM PROTECTED AMINO ACIDS AND PEPTIDES BY CATHODIC REDUCTION
Khalifa, M. Hassen,Rieker, Anton
, p. 1027 - 1030 (2007/10/02)
Amino acids and peptide esters protected by the PChd group can be deprotected cathodically under mild conditions.
