Literature DB >> 21311737

Synthesis of Berberine-Efflux Pump Inhibitor Hybrid Antibacterials.

John B Bremner1, Michael J Kelso.   

Abstract

This paper reports the compact synthesis of two isomeric dual-action hybrid antimicrobials where the 13-position of the antibacterial berberine has been linked via 3'- and 4'-methylene bridges to INF55 (5-nitro-2-phenylindole), an inhibitor of the bacterial NorA multidrug-resistance pump.

Entities:  

Year:  2010        PMID： 21311737      PMCID： PMC3035389          DOI： 10.1080/00397910903457415

Source DB:  PubMed          Journal:  Synth Commun        ISSN： 0039-7911            Impact factor:   2.007


  9 in total

1.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

2.  Conjugating berberine to a multidrug efflux pump inhibitor creates an effective antimicrobial.

Authors:  Anthony R Ball; Gabriele Casadei; Siritron Samosorn; John B Bremner; Frederick M Ausubel; Terence I Moy; Kim Lewis
Journal:  ACS Chem Biol       Date:  2006-10-24       Impact factor: 5.100

3.  Synthesis and evaluation of fluoroquinolone derivatives as substrate-based inhibitors of bacterial efflux pumps.

Authors:  Nadezhda German; Peng Wei; Glenn W Kaatz; Robert J Kerns
Journal:  Eur J Med Chem       Date:  2008-02-08       Impact factor: 6.514

4.  Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ.

Authors:  Xiang Wang; Benjamin S Lane; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

5.  Synthesis of functionalized 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA efflux pump inhibitors.

Authors:  Siritron Samosorn; John B Bremner; Anthony Ball; Kim Lewis
Journal:  Bioorg Med Chem       Date:  2005-10-03       Impact factor: 3.641

6.  The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity.

Authors:  Tlabo C Leboho; Joseph P Michael; Willem A L van Otterlo; Sandy F van Vuuren; Charles B de Koning
Journal:  Bioorg Med Chem Lett       Date:  2009-07-22       Impact factor: 2.823

7.  Synthesis of fluoren-9-ones via palladium-catalyzed cyclocarbonylation of o-halobiaryls.

Authors:  M A Campo; R C Larock
Journal:  Org Lett       Date:  2000-11-16       Impact factor: 6.005

8.  Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: intelligent design and evolution through the judicious use of structure-guided design and structure-activity relationships.

Authors:  Paul S Charifson; Anne-Laure Grillot; Trudy H Grossman; Jonathan D Parsons; Michael Badia; Steve Bellon; David D Deininger; Joseph E Drumm; Christian H Gross; Arnaud LeTiran; Yusheng Liao; Nagraj Mani; David P Nicolau; Emanuele Perola; Steven Ronkin; Dean Shannon; Lora L Swenson; Qing Tang; Pamela R Tessier; Ski-Kai Tian; Martin Trudeau; Tiansheng Wang; Yunyi Wei; Hong Zhang; Dean Stamos
Journal:  J Med Chem       Date:  2008-08-09       Impact factor: 7.446

9.  Structure-activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus.

Authors:  Joseph I Ambrus; Michael J Kelso; John B Bremner; Anthony R Ball; Gabriele Casadei; Kim Lewis
Journal:  Bioorg Med Chem Lett       Date:  2008-07-02       Impact factor: 2.823
  9 in total
  5 in total

Review 1.  Strategies to potentiate antimicrobial photoinactivation by overcoming resistant phenotypes.

Authors:  Domingo Mariano Adolfo Vera; Mark H Haynes; Anthony R Ball; Tianhong Dai; Christos Astrakas; Michael J Kelso; Michael R Hamblin; George P Tegos
Journal:  Photochem Photobiol       Date:  2012-02-13       Impact factor: 3.421

2.  Berberine-INF55 (5-nitro-2-phenylindole) hybrid antimicrobials: effects of varying the relative orientation of the berberine and INF55 components.

Authors:  Danuta Tomkiewicz; Gabriele Casadei; Jonah Larkins-Ford; Terence I Moy; James Garner; John B Bremner; Frederick M Ausubel; Kim Lewis; Michael J Kelso
Journal:  Antimicrob Agents Chemother       Date:  2010-05-24       Impact factor: 5.191

3.  On the Mechanism of Berberine-INF55 (5-Nitro-2-phenylindole) Hybrid Antibacterials.

Authors:  Naveen K Dolla; Chao Chen; Jonah Larkins-Ford; Rajmohan Rajamuthiah; Sakthimala Jagadeesan; Annie L Conery; Frederick M Ausubel; Eleftherios Mylonakis; John B Bremner; Kim Lewis; Michael J Kelso
Journal:  Aust J Chem       Date:  2015       Impact factor: 1.321

4.  Synthesis and structural characterization of 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride.

Authors:  John B Bremner; Siritron Samosorn; Brian W Skelton; Allan H White
Journal:  Molecules       Date:  2011-09-06       Impact factor: 4.411

Review 5.  Structural modifications of berberine and their binding effects towards polymorphic deoxyribonucleic acid structures: A review.

Authors:  Lanlan Fu; Jiajia Mou; Yanru Deng; Xiaoliang Ren
Journal:  Front Pharmacol       Date:  2022-08-09       Impact factor: 5.988
  5 in total

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