Literature DB >> 21752646

Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity.

Seth Daly1, Kathryn Hayden, Indranil Malik, Nikki Porch, Hong Tang, Snezna Rogelj, Liliya V Frolova, Katrina Lepthien, Alexander Kornienko, Igor V Magedov.   

Abstract

A novel reaction of indole with aryldiazonium salts leading to the formation of 2-aryl-3-(arylazo)indoles was discovered. The products were found to possess potent anti-MRSA and anti-LLVRE activities. The SAR studies indicate that the potentially metabolically labile azo functionality can be replaced with ether oxygen and thioether sulfur atoms without any loss of activity.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21752646      PMCID： PMC3233240          DOI： 10.1016/j.bmcl.2011.06.081

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  15 in total

1.  Structure-activity relationships to some antifungal indoles.

Authors:  W H Dekker; H A Selling; J C Overeem
Journal:  J Agric Food Chem       Date:  1975 Jul-Aug       Impact factor: 5.279

2.  Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization.

Authors:  Neil P Grimster; Carolyn Gauntlett; Christopher R A Godfrey; Matthew J Gaunt
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-13       Impact factor: 15.336

3.  Simplified agar plate method for quantifying viable bacteria.

Authors:  B D Jett; K L Hatter; M M Huycke; M S Gilmore
Journal:  Biotechniques       Date:  1997-10       Impact factor: 1.993

4.  Bottromycin derivatives: efficient chemical modifications of the ester moiety and evaluation of anti-MRSA and anti-VRE activities.

Authors:  Yutaka Kobayashi; Maki Ichioka; Tomoyasu Hirose; Kenichiro Nagai; Atsuko Matsumoto; Hidehiro Matsui; Hideaki Hanaki; Rokuro Masuma; Yoko Takahashi; Satoshi Omura; Toshiaki Sunazuka
Journal:  Bioorg Med Chem Lett       Date:  2010-08-18       Impact factor: 2.823

5.  A practical synthesis of alpha-aryl methyl ketones via a transition-metal-free Meerwein arylation.

Authors:  Carmela Molinaro; Jeffrey Mowat; Francis Gosselin; Paul D O'Shea; Jean-François Marcoux; Rémy Angelaud; Ian W Davies
Journal:  J Org Chem       Date:  2007-01-31       Impact factor: 4.354

6.  Structural simplification of bioactive natural products with multicomponent synthesis. 3. Fused uracil-containing heterocycles as novel topoisomerase-targeting agents.

Authors:  Nikolai M Evdokimov; Severine Van Slambrouck; Petra Heffeter; Lee Tu; Benjamin Le Calvé; Delphine Lamoral-Theys; Carla J Hooten; Pavel Y Uglinskii; Snezna Rogelj; Robert Kiss; Wim F A Steelant; Walter Berger; Jeremy J Yang; Cristian G Bologa; Alexander Kornienko; Igor V Magedov
Journal:  J Med Chem       Date:  2011-03-09       Impact factor: 7.446

Review 7.  Invasive community-associated MRSA infections: epidemiology and antimicrobial management.

Authors:  Solen Pichereau; Warren E Rose
Journal:  Expert Opin Pharmacother       Date:  2010-10-19       Impact factor: 3.889

Review 8.  Vancomycin-resistant enterococci (VRE): transmission and control.

Authors:  Evelina Tacconelli; Maria A Cataldo
Journal:  Int J Antimicrob Agents       Date:  2007-12-31       Impact factor: 5.283

9.  Inhibitory and resistance-modifying potential of plant-based alkaloids against methicillin-resistant Staphylococcus aureus (MRSA).

Authors:  Mastura Mohtar; Saiful Azmi Johari; Abdul Rashid Li; Mazurah Mohamed Isa; Shuhaimi Mustafa; Abdul Manaf Ali; Dayang Fredalina Basri
Journal:  Curr Microbiol       Date:  2009-05-28       Impact factor: 2.188

10.  Synthesis and structure-activity relationship of dicationic diaryl ethers as novel potent anti-MRSA and anti-VRE agents.

Authors:  Laixing Hu; Maureen L Kully; David W Boykin; Norman Abood
Journal:  Bioorg Med Chem Lett       Date:  2009-06-25       Impact factor: 2.823
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  8 in total

1.  Antiproliferative activity of 2,3-disubstituted indoles toward apoptosis-resistant cancers cells.

Authors:  Igor V Magedov; Florence Lefranc; Liliya V Frolova; Laetitia Moreno Y Banuls; Amanda S Peretti; Snezna Rogelj; Véronique Mathieu; Robert Kiss; Alexander Kornienko
Journal:  Bioorg Med Chem Lett       Date:  2013-04-08       Impact factor: 2.823

2.  Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors:  Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-08       Impact factor: 15.336

3.  Photoactivated 2,3-distyrylindoles kill multi-drug resistant bacteria.

Authors:  Leslie Edwards; Danielle Turner; Cody Champion; Megha Khandelwal; Kailee Zingler; Cassidy Stone; Ruwini D Rajapaksha; Jing Yang; Mahinda I Ranasinghe; Alexander Kornienko; Liliya V Frolova; Snezna Rogelj
Journal:  Bioorg Med Chem Lett       Date:  2018-04-03       Impact factor: 2.823

4.  Photo-physical properties of substituted 2,3-distyryl indoles: Spectroscopic, computational and biological insights.

Authors:  Ruwini D Rajapaksha; Danielle N Turner; Jade Vigil; Liliya V Frolova; Jeff Altig; Snezna Rogelj; Mahinda I Ranasinghe
Journal:  J Photochem Photobiol A Chem       Date:  2019-03-06       Impact factor: 4.291

5.  Synergistic action of substituted indole derivatives and clinically used antibiotics against drug-resistant bacteria.

Authors:  Danielle N Turner; Leslie Edwards; Alexander Kornienko; Liliya V Frolova; Snezna Rogelj
Journal:  Future Microbiol       Date:  2020-06-02       Impact factor: 3.165

6.  Mild and selective base-free C-H arylation of heteroarenes: experiment and computation.

Authors:  Hannes P L Gemoets; Indrek Kalvet; Alexander V Nyuchev; Nico Erdmann; Volker Hessel; Franziska Schoenebeck; Timothy Noël
Journal:  Chem Sci       Date:  2016-09-05       Impact factor: 9.825

7.  Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.

Authors:  Mindaugas Šiaučiulis; Selma Sapmaz; Alexander P Pulis; David J Procter
Journal:  Chem Sci       Date:  2017-11-17       Impact factor: 9.825

8.  Exploration of C-H and N-H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines.

Authors:  Michael Ghobrial; Marko D Mihovilovic; Michael Schnürch
Journal:  Beilstein J Org Chem       Date:  2014-09-15       Impact factor: 2.883
  8 in total

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