New tetracyclic tetrahydro-beta-carbolines as tryptophan-derived peptidomimetics.
The Pictet-Spengler reaction is known as a useful tool for the synthesis of constrained analogs of tryptophan. Herein, we present the further cyclization of 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid methyl esters with 1-(1'-aminoalkyl) side chain. These transformations lead to heterocyclic structures which can find useful applications in medicinal chemistry as peptide mimetics.
Pulka
Karolina
K
Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093, Warsaw, Poland. karola@chem.uw.edu.pl
Feytens
Debby
D
Misicka
Aleksandra
A
Tourwé
Dirk
D
D000596:Amino Acids / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry*; D048289:Imidazolidines / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry*; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry
D000596:Amino Acids; D002243:Carbolines; D048289:Imidazolidines; D010455:Peptides; D010879:Piperazines; D014364:Tryptophan