Literature DB >> 21674109

Flustramine inspired synthesis and biological evaluation of pyrroloindoline triazole amides as novel inhibitors of bacterial biofilms.

Cynthia Bunders1, John Cavanagh, Christian Melander.   

Abstract

Anti-biofilm agents have been developed based upon the flustramine family of alkaloids isolated from Flustra foliacea. A Garg interrupted Fischer indolization reaction was employed to access a core pyrroloindoline scaffold that was subsequently employed to create a pyrroloindoline triazole amide library. Screening for the ability to modulate biofilm formation against strains of Gram-positive and Gram-negative bacteria identified several compounds with low micromolar, non-toxic IC(50) values.

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Year:  2011        PMID: 21674109      PMCID: PMC3428232          DOI: 10.1039/c1ob05605k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  22 in total

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Journal:  Science       Date:  1999-05-21       Impact factor: 47.728

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Review 3.  Chemical countermeasures for the control of bacterial biofilms: effective compounds and promising targets.

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Review 4.  Bacterial quorum sensing: signals, circuits, and implications for biofilms and disease.

Authors:  Arul Jayaraman; Thomas K Wood
Journal:  Annu Rev Biomed Eng       Date:  2008       Impact factor: 9.590

5.  Quorum-sensing signals indicate that cystic fibrosis lungs are infected with bacterial biofilms.

Authors:  P K Singh; A L Schaefer; M R Parsek; T O Moninger; M J Welsh; E P Greenberg
Journal:  Nature       Date:  2000-10-12       Impact factor: 49.962

6.  Environmental factors affecting indole production in Escherichia coli.

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Journal:  Res Microbiol       Date:  2010-12-08       Impact factor: 3.992

7.  The facile preparation of primary and secondary amines via an improved Fukuyama-Mitsunobu procedure. Application to the synthesis of a lung-targeted gene delivery agent.

Authors:  Cristina Guisado; Jodie E Waterhouse; Wayne S Price; Michael R Jorgensen; Andrew D Miller
Journal:  Org Biomol Chem       Date:  2005-02-15       Impact factor: 3.876

8.  Indole cell signaling occurs primarily at low temperatures in Escherichia coli.

Authors:  Jintae Lee; Xue-Song Zhang; Manjunath Hegde; William E Bentley; Arul Jayaraman; Thomas K Wood
Journal:  ISME J       Date:  2008-06-05       Impact factor: 10.302

9.  Multidrug-resistant Acinetobacter extremity infections in soldiers.

Authors:  Kepler A Davis; Kimberly A Moran; C Kenneth McAllister; Paula J Gray
Journal:  Emerg Infect Dis       Date:  2005-08       Impact factor: 6.883

10.  Indole is an inter-species biofilm signal mediated by SdiA.

Authors:  Jintae Lee; Arul Jayaraman; Thomas K Wood
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  13 in total

Review 1.  Small molecule control of bacterial biofilms.

Authors:  Roberta J Worthington; Justin J Richards; Christian Melander
Journal:  Org Biomol Chem       Date:  2012-10-07       Impact factor: 3.876

2.  2-Aminopyrimidine as a novel scaffold for biofilm modulation.

Authors:  Erick A Lindsey; Roberta J Worthington; Cristina Alcaraz; Christian Melander
Journal:  Org Biomol Chem       Date:  2012-02-02       Impact factor: 3.876

3.  Natural products as inspiration for the development of bacterial antibiofilm agents.

Authors:  Roberta J Melander; Akash K Basak; Christian Melander
Journal:  Nat Prod Rep       Date:  2020-07-01       Impact factor: 13.423

4.  Controlling bacterial behavior with indole-containing natural products and derivatives.

Authors:  Roberta J Melander; Marine J Minvielle; Christian Melander
Journal:  Tetrahedron       Date:  2014-09-16       Impact factor: 2.457

5.  Hijacking the Bacterial Circuitry of Biofilm Processes via Chemical "Hot-Wiring": An Under-explored Avenue for Therapeutic Development.

Authors:  Ingrid K Wilt; Taylor P A Hari; William M Wuest
Journal:  ACS Infect Dis       Date:  2019-04-19       Impact factor: 5.084

6.  Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

Authors:  Alex W Schammel; Grace Chiou; Neil K Garg
Journal:  Org Lett       Date:  2012-08-20       Impact factor: 6.005

7.  Evaluation of ethyl N-(2-phenethyl) carbamate analogues as biofilm inhibitors of methicillin resistant Staphylococcus aureus.

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Journal:  Org Biomol Chem       Date:  2016-07-12       Impact factor: 3.876

8.  Indole/triazole conjugates are selective inhibitors and inducers of bacterial biofilms.

Authors:  Marine J Minvielle; Cynthia A Bunders; Christian Melander
Journal:  Medchemcomm       Date:  2013-06-01       Impact factor: 3.597

9.  Simultaneous ultrasound- and microwave-assisted one-pot 'click' synthesis of 3-formyl-indole clubbed 1,2,3-triazole derivatives and their biological evaluation.

Authors:  Jaydeep A Mokariya; Anirudhdha G Kalola; Pratibha Prasad; Manish P Patel
Journal:  Mol Divers       Date:  2021-04-08       Impact factor: 2.943

10.  Formation of Pyrroloindolines via the Alkylation of Tryptamines with Trichloroacetimidates.

Authors:  Bhaskar D Joshi; John D Chisholm
Journal:  Tetrahedron Lett       Date:  2021-07-01       Impact factor: 2.032

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