Literature DB >> 21113437

Two-Steps Hantzsch Based Macrocyclization Approach for the Synthesis of Thiazole Containing Cyclopeptides.

Adel Nefzi1, Sergey Arutyunyan, Jason E Fenwick.   

Abstract

Macrocyclization via an efficient high-yielding solid-phase intramolecular thioalkylation reaction is described. The reaction of S-nucleophiles with newly generated N-terminal 4-chloromethyl thiazoles led to the desired macrocyclization products 5 in high purities and good overall yields.

Entities:  

Year:  2010        PMID： 21113437      PMCID： PMC2989683     

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  33 in total

Review 1.  Lantibiotics and microcins: polypeptides with unusual chemical diversity.

Authors:  R W Jack; G Jung
Journal:  Curr Opin Chem Biol       Date:  2000-06       Impact factor: 8.822

2.  Solid-phase SN2 macrocyclization reactions to form beta-turn mimics.

Authors:  Y Feng; M Pattarawarapan; Z Wang; K Burgess
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

Review 3.  Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads.

Authors:  V J Hruby; P M Balse
Journal:  Curr Med Chem       Date:  2000-09       Impact factor: 4.530

4.  Solid-Phase Synthesis of 2-Aminothiazoles.

Authors:  Patrick C. Kearney; Monica Fernandez; John A. Flygare
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

5.  Synthesis of cyclic peptides by ring-closing metathesis.

Authors:  J F Reichwein; C Versluis; R M Liskamp
Journal:  J Org Chem       Date:  2000-09-22       Impact factor: 4.354

Review 6.  Designing peptide receptor agonists and antagonists.

Authors:  Victor J Hruby
Journal:  Nat Rev Drug Discov       Date:  2002-11       Impact factor: 84.694

Review 7.  Design of beta-turn based therapeutic agents.

Authors:  K Suat Kee; Seetharama D S Jois
Journal:  Curr Pharm Des       Date:  2003       Impact factor: 3.116

8.  Cyclic Dipeptides. 3.(1) Synthesis of Methyl (R)-6-[(tert-Butoxycarbonyl)amino]-4,5,6,7- tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3-carboxylate and Its Hexahydro Analogues: Elaboration of a Novel Dual ACE/NEP Inhibitor.

Authors:  Angela Crescenza; Maurizio Botta; Federico Corelli; Antonello Santini; Andrea Tafi
Journal:  J Org Chem       Date:  1999-04-30       Impact factor: 4.354

9.  Stereoselective synthesis of novel dipeptide beta-turn mimetics targeting melanocortin peptide receptors.

Authors:  Junyi Zhang; Chiyi Xiong; Jinfa Ying; Wei Wang; Victor J Hruby
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

10.  Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling.

Authors:  Markus Kaiser; Carlo Siciliano; Irmgard Assfalg-Machleidt; Michael Groll; Alexander G Milbradt; Luis Moroder
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005
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  1 in total

1.  Parallel Synthesis of Structurally Diverse Aminobenzimidazole Tethered Sultams and Benzothiazepinones.

Authors:  Sureshbabu Dadiboyena; Adel Nefzi
Journal:  Tetrahedron Lett       Date:  2012-12-19       Impact factor: 2.415
  1 in total

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