Literature DB >> 12425603

Solid-supported synthesis of putative peptide beta-turn mimetics via Ugi reaction for diketopiperazine formation.

Adam Golebiowski1, Julita Jozwik, Sean R Klopfenstein, Anny-Odile Colson, Arthur L Grieb, Anne F Russell, Vinit L Rastogi, Conrad F Diven, David E Portlock, Jack J Chen.   

Abstract

The scope and limitations of the solid-supported synthesis of a bicyclic diketopiperazine, an internal, putative peptide beta-turn mimetic, are presented. The 4CC multicomponent Ugi reaction of alpha-N-Boc-diaminopropionic acid resin ester (an amine input), optically active alpha-bromoacid, aldehyde, and isocyanide is the key step in the proposed synthetic protocol. Application of cyclitive cleavage as the final step led to desired products in high purity.

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Year:  2002        PMID: 12425603     DOI: 10.1021/cc020029u

Source DB:  PubMed          Journal:  J Comb Chem        ISSN: 1520-4766


  8 in total

1.  Defining scaffold geometries for interacting with proteins: geometrical classification of secondary structure linking regions.

Authors:  Tran T Tran; Christina Kulis; Steven M Long; Darryn Bryant; Peter Adams; Mark L Smythe
Journal:  J Comput Aided Mol Des       Date:  2010-09-23       Impact factor: 3.686

2.  Solid-phase synthesis of N-substituted pyrrolidinone-tethered N-substituted piperidines via Ugi reaction.

Authors:  Zhang Liu; Adel Nefzi
Journal:  J Comb Chem       Date:  2010-07-12

Review 3.  Solid-phase and microwave-assisted syntheses of 2,5-diketopiperazines: small molecules with great potential.

Authors:  Jennifer C O'Neill; Helen E Blackwell
Journal:  Comb Chem High Throughput Screen       Date:  2007-12       Impact factor: 1.339

4.  Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics.

Authors:  Craig A Hutton; Paul A Bartlett
Journal:  J Org Chem       Date:  2007-08-08       Impact factor: 4.354

Review 5.  Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics.

Authors:  Gijs Koopmanschap; Eelco Ruijter; Romano Va Orru
Journal:  Beilstein J Org Chem       Date:  2014-03-04       Impact factor: 2.883

Review 6.  Isocyanide Multicomponent Reactions on Solid Phase: State of the Art and Future Application.

Authors:  Naděžda Cankařová; Viktor Krchňák
Journal:  Int J Mol Sci       Date:  2020-12-01       Impact factor: 5.923

7.  Synthesis of Chromeno[3,4-b]piperazines by an Enol-Ugi/Reduction/Cyclization Sequence.

Authors:  Ana Bornadiego; Ana G Neo; Carlos F Marcos
Journal:  Molecules       Date:  2021-02-27       Impact factor: 4.411

Review 8.  Heterocycles as a Peptidomimetic Scaffold: Solid-Phase Synthesis Strategies.

Authors:  Aizhan Abdildinova; Mark J Kurth; Young-Dae Gong
Journal:  Pharmaceuticals (Basel)       Date:  2021-05-10
  8 in total

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