Literature DB >> 25960576

Preparation of azidoaryl- and azidoalkyloxazoles for click chemistry.

Catherine M Loner1, Frederick A Luzzio2, Donald R Demuth1.   

Abstract

A series of azidoaryl- and azidoalkyl(diphenyl)oxazole scaffolds were warranted for biofilm inhibition studies. Cyclization of azidoaryl- or azidoalkyl esters of benzoin with ammonium acetate in acetic acid gives 2-azidoaryl- or 2-azidoalkyl-4,5-diphenyloxazoles. The azidoaryl esters are prepared from the corresponding azidocarboxylic acids/acid chlorides while the azidoalkyl esters are prepared from the corresponding haloalkyl esters.

Entities:  

Keywords:  Azides; Biofilms; Click chemistry; Oxazoles; Peptidomimetics

Year:  2012        PMID： 25960576      PMCID： PMC4422068          DOI： 10.1016/j.tetlet.2012.08.032

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  18 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

2.  Synthesis of sansalvamide A peptidomimetics: triazole, oxazole, thiazole, and pseudoproline containing compounds.

Authors:  Melinda R Davis; Erinprit K Singh; Hendra Wahyudi; Leslie D Alexander; Joseph B Kunicki; Lidia A Nazarova; Kelly A Fairweather; Andrew M Giltrap; Katrina A Jolliffe; Shelli R McAlpine
Journal:  Tetrahedron       Date:  2012-01-28       Impact factor: 2.457

Review 3.  Click chemistry, a powerful tool for pharmaceutical sciences.

Authors:  Christopher D Hein; Xin-Ming Liu; Dong Wang
Journal:  Pharm Res       Date:  2008-05-29       Impact factor: 4.200

Review 4.  Oral biofilms: emerging concepts in microbial ecology.

Authors:  S Filoche; L Wong; C H Sissons
Journal:  J Dent Res       Date:  2010-01       Impact factor: 6.116

5.  Three ring posttranslational circuses: insertion of oxazoles, thiazoles, and pyridines into protein-derived frameworks.

Authors:  Christopher T Walsh; Steven J Malcolmson; Travis S Young
Journal:  ACS Chem Biol       Date:  2012-01-17       Impact factor: 5.100

6.  Structural characterization of peptide-mediated inhibition of Porphyromonas gingivalis biofilm formation.

Authors:  Carlo Amorin Daep; Deanna M James; Richard J Lamont; Donald R Demuth
Journal:  Infect Immun       Date:  2006-10       Impact factor: 3.441

7.  Anti-AIDS agents 88. Anti-HIV conjugates of betulin and betulinic acid with AZT prepared via click chemistry.

Authors:  Ibrahim D Bori; Hsin-Yi Hung; Keduo Qian; Chin-Ho Chen; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Tetrahedron Lett       Date:  2012-04-11       Impact factor: 2.415

8.  Organic azides: an exploding diversity of a unique class of compounds.

Authors:  Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

9.  Interaction of Porphyromonas gingivalis with oral streptococci requires a motif that resembles the eukaryotic nuclear receptor box protein-protein interaction domain.

Authors:  Carlo Amorin Daep; Richard J Lamont; Donald R Demuth
Journal:  Infect Immun       Date:  2008-05-12       Impact factor: 3.441

10.  Efficient synthesis of azide-bearing cofactor mimics.

Authors:  Lindsay R Comstock; Scott R Rajski
Journal:  J Org Chem       Date:  2004-02-20       Impact factor: 4.354
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  7 in total

1.  Synthesis of extended oxazoles II: Reaction manifold of 2-(halomethyl)-4,5-diaryloxazoles.

Authors:  Pravin C Patil; Frederick A Luzzio
Journal:  Tetrahedron Lett       Date:  2016-02-17       Impact factor: 2.415

2.  1,2,3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation.

Authors:  Pravin C Patil; Jinlian Tan; Donald R Demuth; Frederick A Luzzio
Journal:  Bioorg Med Chem       Date:  2016-09-07       Impact factor: 3.641

3.  Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds.

Authors:  Pravin C Patil; Frederick A Luzzio; Donald R Demuth
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Chemoenzymatic route to stereodefined 2-(azidophenyl)oxazolines for click chemistry.

Authors:  Paige J Monsen; Frederick A Luzzio
Journal:  Tetrahedron Lett       Date:  2020-12-17       Impact factor: 2.415

5.  α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones.

Authors:  Liquan Tan; Cui Chen; Weibing Liu
Journal:  Beilstein J Org Chem       Date:  2017-06-06       Impact factor: 2.883

6.  'Second-generation' 1,2,3-triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation.

Authors:  Pravin C Patil; Jinlian Tan; Donald R Demuth; Frederick A Luzzio
Journal:  Medchemcomm       Date:  2019-01-15       Impact factor: 3.597

7.  In Vitro and In Vivo Activity of Peptidomimetic Compounds That Target the Periodontal Pathogen Porphyromonas gingivalis.

Authors:  Jinlian Tan; Pravin C Patil; Frederick A Luzzio; Donald R Demuth
Journal:  Antimicrob Agents Chemother       Date:  2018-06-26       Impact factor: 5.191
  7 in total

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