642073-57-2

Upstream product

• 577-19-5 2-nitrophenyl bromide 
• 115666-21-2 7-bromo-1 H-indole-3-carbaldehyde 
• 1026562-19-5 7-bromo-3-bromomethyl-indole-1-carboxylic acid tert-butyl ester 
• 642073-51-6 7-bromo-N-(tert-butyloxycarbonyl)-3-(hydroxymethyl)indole 
• 27601-29-2 t-butyloxycarbonyl-O-benzyl-L-tyrosine hydroxysuccinimide ester 
• 51417-51-7 7-bromo-1H-indole 
• 642073-54-9 N-Boc-3-iodo-Tyr(Bzl)-Ala-OMe 
• 59095-84-0 N-Boc-Tyr(Bzl)-Ala-OMe 
• 642073-52-7 (7-bromo)Trp(Boc)-OtBu 
• 700376-95-0 N-Boc-3-iodo-Tyr(Bn)-Ala-OH 

Relevant academic research and scientific papers

Linear TMC-95-based proteasome inhibitors

We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and

COMPOUNDS USEFUL AS MODULATORS OF THE PROTEASOME ACTIVITY

The present invention relates to the use of compounds of the following general formula (I): wherein no is 0 or 1, and when no is 1, X = CH2 or X = NCH2C6H5; R1 is OH, or a OR10 group, or a group of formula NH-(CH2)n1-R11; R2 is H, or an alkyl group, or a group of formula (CH2)n2-(CO)n3-NR13R14; R3 is H, or an alkyl group; R4 is H, or Boc, or Z; R5 is H, or Boc, or Z ; R6 is a OR16 group; R7 and R8 are H, or a halogen atom, as modulators of the proteasome activity, in the frame of the preparation of a medicament useful for the prevention or treatment of diseases wherein the proteasome is involved, or the preparation of cosmetic compositions, or of phytosanitary compositions.

Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A

The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(O)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.