Carbonylation as a novel method for the assembly of pyrazine based oligoamide alpha-helix mimetics.

The design and synthesis of oligoamide α-helix peptidomimetics is reported. The oligoamide type systems are prepared in a modular fashion by coupling the monomers using palladium-catalyzed carbonylation chemistry. This enabled us to use substrates with a low nucleophilicity, leading to previously unreported pyrazine based oligoamide α-helix mimetics. The proof of principle is given by synthesizing a small set of compounds. Various end-capping groups were introduced and also a mixed multimer was successfully prepared.

• Publication year

  2017

• Venue

  Organic and biomolecular chemistry

• Publication date

  2017-01-04

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c6ob02358dPMID 27910980
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• How Beyond Rule of 5 Drugs and Clinical Candidates Bind to Their Targets.

  2016cited by this paper
• Low-cost instant CO generation at room temperature using formic acid, mesyl chloride and triethylamine

  2016cited by this paper
• Synthesis of highly functionalized oligobenzamide proteomimetic foldamers by late stage introduction of sensitive groups† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6ob00078a Click here for additional data file.

  2016cited by this paper
• Synthesis and screening of small-molecule α-helix mimetic libraries targeting protein-protein interactions.

  2015cited by this paper
• Stereocontrolled protein surface recognition using chiral oligoamide proteomimetic foldamers† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03559c Click here for additional data file.

  2015cited by this paper
• Design, synthesis and conformational analyses of bifacial benzamide based foldamers

  2015cited by this paper
• Amphiphilic oligoamide α-helix peptidomimetics inhibit islet amyloid polypeptide aggregation

  2015cited by this paper
• Small-molecule inhibitors of protein-protein interactions: progressing toward the reality.

  2014cited by this paper
• α-Helix mimetics: outwards and upwards.

  2014cited by this paper
• Targeting protein-protein interaction by small molecules.

  2014cited by this paper
• Studies on the regioselective nucleophilic aromatic substitution (S(N)Ar) reaction of 2-substituted 3,5-dichloropyrazines.

  2013cited by this paper
• Solid-Phase Methodology for Synthesis of O-Alkylated Aromatic Oligoamide Inhibitors of α-Helix-Mediated Protein–Protein Interactions

  2013cited by this paper
• Peptidomimetic targeting of critical androgen receptor–coregulator interactions in prostate cancer

  2013cited by this paper
• Design and Synthesis of Oligoamide-Based Double α-Helix Mimetics

  2013cited by this paper
• Aromatic Oligoamide Foldamers with a "Wet Edge" as Inhibitors of the α- Helix-Mediated p53-hDM2 Protein-Protein Interaction

  2013cited by this paper
• Protein interface pharmacophore mapping tools for small molecule protein: protein interaction inhibitor discovery.

  2013cited by this paper
• Evaluating minimalist mimics by exploring key orientations on secondary structures (EKOS).

  2013cited by this paper
• Inhibition of α-helix-mediated protein-protein interactions using designed molecules.

  2013cited by this paper
• An anthraquinone scaffold for putative, two-face Bim BH3 α-helix mimic.

  2012cited by this paper
• Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

  2012cited by this paper
• Synthesis of the novel trimeric benzamides—potential inhibitors of protein–protein interactions

  2012cited by this paper
• Relaxation of the rigid backbone of an oligoamide-foldamer-based α-helix mimetic: identification of potent Bcl-xL inhibitors.

  2012cited by this paper
• 2-O-alkylated para-benzamide α-helix mimetics: the role of scaffold curvature.

  2012cited by this paper
• Assessing helical protein interfaces for inhibitor design.

  2011cited by this paper
• Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations.

  2011cited by this paper
• N-alkylated oligoamide alpha-helical proteomimetics.

  2010cited by this paper
• Novel amphiphilic alpha-helix mimetics based on a bis-benzamide scaffold.

  2009cited by this paper
• Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.

  2009cited by this paper
• Synthesis of functionalised aromatic oligamide rods.

  2008cited by this paper
• Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.

  2008cited by this paper
• Controlling curvature in a family of oligoamide alpha-helix mimetics.

  2008cited by this paper
• Helix mimetics as inhibitors of the interaction of the estrogen receptor with coactivator peptides.

  2007cited by this paper
• Heterocyclic alpha-helix mimetics for targeting protein-protein interactions.

  2007cited by this paper
• Heterocyclic α-helix mimetics for targeting protein-protein interactions

  2007cited by this paper
• Simplification of the Mitsunobu reaction. Di-p-chlorobenzyl azodicarboxylate: a new azodicarboxylate.

  2006cited by this paper
• Substituted 1,4‐Benzodiazepine‐2,5‐diones as α‐Helix Mimetic Antagonists of the HDM2‐p53 Protein–Protein Interaction

  2006cited by this paper
• Design and modular parallel synthesis of a MCR derived alpha-helix mimetic protein-protein interaction inhibitor scaffold.

  2006cited by this paper
• Terphenyl-Based Bak BH3 α-Helical Proteomimetics as Low-Molecular-Weight Antagonists of Bcl-xL

  2005cited by this paper
• Terphenyl-based helical mimetics that disrupt the p53/HDM2 interaction.

  2005cited by this paper
• Terphenyl-Based Bak BH3 alpha-helical proteomimetics as low-molecular-weight antagonists of Bcl-xL.

  2005cited by this paper
• Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position

  2004cited by this paper
• Potent and selective farnesyl transferase inhibitors.

  2004cited by this paper
• Design and application of an alpha-helix-mimetic scaffold based on an oligoamide-foldamer strategy: antagonism of the Bak BH3/Bcl-xL complex.

  2003cited by this paper
• Synthesis and cytotoxicity evaluation of novel indolylpyrimidines and indolylpyrazines as potential antitumor agents.

  2001cited by this paper
• Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998

  1999cited by this paper
• Sequential N-Arylation of Primary Amines as a Route To Alkyldiarylamines

  1999cited by this paper
• Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen

  1998cited by this paper
• A Simple One-Pot Preparation of N,N’-Unsymmetrical Ureas from N-Boc Protected Primary Anilines and Amines

  1996cited by this paper
• Bioisosterism: A Rational Approach in Drug Design.

  1996cited by this paper
• A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines

  1995cited by this paper
• A hot spot of binding energy in a hormone-receptor interface

  1995cited by this paper

• Unnatural foldamers as inhibitors of Aβ aggregation via stabilizing the Aβ helix

  2025cites this paper
• Evolution in non-peptide α-helix mimetics on the road to effective protein-protein interaction modulators.

  2020cites this paper
• Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity.

  2019cites this paper
• Peptidomimetics: A Synthetic Tool for Inhibiting Protein–Protein Interactions in Cancer

  2019cites this paper
• Synthesis and structure-activity relationships of 3,5-disubstituted-pyrrolo[2,3-b]pyridines as inhibitors of adaptor associated kinase 1 (AAK1) with antiviral activity

  2019cites this paper
• Using Peptidomimetics and Constrained Peptides as Valuable Tools for Inhibiting Protein–Protein Interactions

  2018cites this paper
• Intramolecular Carbonylative C–H Functionalization of 1,2,3‐ Triazoles for the Synthesis of Triazolo[1,5‐a]indolones

  2017cites this paper
• Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates.

  2017cites this paper