Literature DB >> 19529982

New tetracyclic tetrahydro-beta-carbolines as tryptophan-derived peptidomimetics.

Karolina Pulka1, Debby Feytens, Aleksandra Misicka, Dirk Tourwé.   

Abstract

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.

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Year:  2009        PMID： 19529982     DOI： 10.1007/s11030-009-9151-y

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  16 in total

1.  Conformationally restricted PACAP27 analogues incorporating type II/II' IBTM beta-turn mimetics. Synthesis, NMR structure determination, and binding affinity.

Authors:  R González-Muñiz; M Martín-Martínez; C Granata; E de Oliveira; C M Santiveri; C González; D Frechilla; R Herranz; M T García-López; J Del Río; M Angeles Jiménez; D Andreu
Journal:  Bioorg Med Chem       Date:  2001-12       Impact factor: 3.641

2.  Solid-phase synthesis of 1,2,3, 4-tetrahydro-beta-carboline-containing peptidomimetics.

Authors:  X Li; L Zhang; W Zhang; S E Hall; J P Tam
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

Review 3.  Exploring Ramachandran and chi space: conformationally constrained amino acids and peptides in the design of bioactive polypeptide ligands.

Authors:  S M Cowell; Y S Lee; J P Cain; V J Hruby
Journal:  Curr Med Chem       Date:  2004-11       Impact factor: 4.530

4.  Solid-phase parallel synthesis of natural product-like diaza-bridged heterocycles through Pictet-Spengler intramolecular cyclization.

Authors:  Sung-Chan Lee; Seung Bum Park
Journal:  J Comb Chem       Date:  2006 Jan-Feb

5.  Solid-phase synthesis of multiple classes of peptidomimetics from versatile resin-bound aldehyde intermediates.

Authors:  William L Scott; Jacek G Martynow; John C Huffman; Martin J O'Donnell
Journal:  J Am Chem Soc       Date:  2007-05-16       Impact factor: 15.419

6.  Effects of the incorporation of IBTM beta-turn mimetics into the dipeptoid CCK(1) receptor agonist PD 170292.

Authors:  Mercedes Martín-Martínez; Miriam Latorre; M Teresa García-López; Edurne Cenarruzabeitia; Joaquín Del Río; Rosario González-Muñiz
Journal:  Bioorg Med Chem Lett       Date:  2002-01-21       Impact factor: 2.823

7.  Affinity and selectivity of matrix metalloproteinase inhibitors: a chemometrical study from the perspective of ligands and proteins.

Authors:  H Matter; W Schwab
Journal:  J Med Chem       Date:  1999-11-04       Impact factor: 7.446

8.  Solid-phase synthesis of tetrahydro-beta-carbolines and tetrahydroisoquinolines by stereoselective intramolecular N-carbamyliminium Pictet-Spengler reactions.

Authors:  Frederik Diness; Jürgen Beyer; Morten Meldal
Journal:  Chemistry       Date:  2006-10-25       Impact factor: 5.236

9.  Combinatorial chemistry: libraries from libraries, the art of the diversity-oriented transformation of resin-bound peptides and chiral polyamides to low molecular weight acyclic and heterocyclic compounds.

Authors:  Adel Nefzi; John M Ostresh; Yongping Yu; Jongping Yu; Richard A Houghten
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

10.  Solid-phase intramolecular N-acyliminium Pictet-Spengler reactions as crossroads to scaffold diversity.

Authors:  Thomas E Nielsen; Morten Meldal
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354
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  2 in total

1.  Synthesis of bis-peptides attached on poly[n]norbornene molecular scaffolds with well-defined relative positions and distances.

Authors:  Muhong Shang; Ronald N Warrener; Douglas N Butler; Yasujiro Murata; Davor Margetić
Journal:  Mol Divers       Date:  2010-09-21       Impact factor: 2.943

Review 2.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
  2 in total

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