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Literature DB >> 20488706

Biological activity of modified and exchanged 2-amino-5-nitrothiazole amide analogues of nitazoxanide.

T Eric Ballard¹, Xia Wang, Igor Olekhnovich, Taylor Koerner, Craig Seymour, Paul S Hoffman, Timothy L Macdonald.

Abstract

Head group analogues of the antibacterial and antiparasitic drug nitazoxanide (NTZ) are presented. A library of 39 analogues was synthesized and assayed for their ability to suppress growth of Helicobacter pylori, Campylobacter jejuni, Clostridium difficile and inhibit NTZ target pyruvate:ferredoxin oxidoreductase (PFOR). Two head groups assayed recapitulated NTZ activity and possessed improved activity over their 2-amino-5-nitrothiazole counterparts, demonstrating that head group modification is a viable route for the synthesis of NTZ-related antibacterial analogues. Copyright 2010 Elsevier Ltd. All rights reserved.

Entities: Chemical Disease Species

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Year: 2010 PMID： 20488706 PMCID： PMC2881195 DOI： 10.1016/j.bmcl.2010.04.126

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

24 in total

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Authors: Herbert M Gilles; Paul S Hoffman
Journal: Trends Parasitol Date: 2002-03

2. A new ferredoxin-dependent carbon reduction cycle in a photosynthetic bacterium.

Authors: M C Evans; B B Buchanan; D I Arnon
Journal: Proc Natl Acad Sci U S A Date: 1966-04 Impact factor: 11.205

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Authors: J Broekhuysen; A Stockis; R L Lins; J De Graeve; J F Rossignol
Journal: Int J Clin Pharmacol Ther Date: 2000-08 Impact factor: 1.366

4. Nitazoxanide inhibits biofilm formation by Staphylococcus epidermidis by blocking accumulation on surfaces.

Authors: Florence Tchouaffi-Nana; T Eric Ballard; Christine H Cary; Timothy L Macdonald; Costi D Sifri; Paul S Hoffman
Journal: Antimicrob Agents Chemother Date: 2010-04-19 Impact factor: 5.191

5. Towards a new therapeutic target: Helicobacter pylori flavodoxin.

Authors: Nunilo Cremades; Marta Bueno; Miguel Toja; Javier Sancho
Journal: Biophys Chem Date: 2005-01-07 Impact factor: 2.352

6. Nitazoxanide, a potential drug for eradication of Helicobacter pylori with no cross-resistance to metronidazole.

Authors: F Mégraud; A Occhialini; J F Rossignol
Journal: Antimicrob Agents Chemother Date: 1998-11 Impact factor: 5.191

7. Comparative clinical studies of nitazoxanide, albendazole and praziquantel in the treatment of ascariasis, trichuriasis and hymenolepiasis in children from Peru.

Authors: Jave Ortiz Juan; Nicholas Lopez Chegne; Gilles Gargala; Loic Favennec
Journal: Trans R Soc Trop Med Hyg Date: 2002 Mar-Apr Impact factor: 2.184

8. Molecular and phylogenetic characterization of pyruvate and 2-ketoisovalerate ferredoxin oxidoreductases from Pyrococcus furiosus and pyruvate ferredoxin oxidoreductase from Thermotoga maritima.

Authors: A Kletzin; M W Adams
Journal: J Bacteriol Date: 1996-01 Impact factor: 3.490

9. Respiratory physiology and energy conservation efficiency of Campylobacter jejuni.

Authors: P S Hoffman; T G Goodman
Journal: J Bacteriol Date: 1982-04 Impact factor: 3.490

10. Enzymes associated with reductive activation and action of nitazoxanide, nitrofurans, and metronidazole in Helicobacter pylori.

Authors: Gary Sisson; Avery Goodwin; Ausra Raudonikiene; Nicky J Hughes; Asish K Mukhopadhyay; Douglas E Berg; Paul S Hoffman
Journal: Antimicrob Agents Chemother Date: 2002-07 Impact factor: 5.191

11 in total

1. Synthesis and antimicrobial evaluation of nitazoxanide-based analogues: identification of selective and broad spectrum activity.

Authors: T Eric Ballard; Xia Wang; Igor Olekhnovich; Taylor Koerner; Craig Seymour; Joseph Salamoun; Michelle Warthan; Paul S Hoffman; Timothy L Macdonald
Journal: ChemMedChem Date: 2010-12-29 Impact factor: 3.466

Review 2. Targeting bacterial membrane function: an underexploited mechanism for treating persistent infections.

Authors: Julian G Hurdle; Alex J O'Neill; Ian Chopra; Richard E Lee
Journal: Nat Rev Microbiol Date: 2011-01 Impact factor: 60.633

3. Thiazolides as novel antiviral agents. 1. Inhibition of hepatitis B virus replication.

Authors: Andrew V Stachulski; Chandrakala Pidathala; Eleanor C Row; Raman Sharma; Neil G Berry; Mazhar Iqbal; Joanne Bentley; Sarah A Allman; Geoffrey Edwards; Alison Helm; Jennifer Hellier; Brent E Korba; J Edward Semple; Jean-Francois Rossignol
Journal: J Med Chem Date: 2011-05-23 Impact factor: 7.446

4. A small molecule screening to detect potential therapeutic targets in human podocytes.

Authors: Eugen Widmeier; Weizhen Tan; Merlin Airik; Friedhelm Hildebrandt
Journal: Am J Physiol Renal Physiol Date: 2016-10-19

5. Synthesis and Antimicrobial Evaluation of Amixicile-Based Inhibitors of the Pyruvate-Ferredoxin Oxidoreductases of Anaerobic Bacteria and Epsilonproteobacteria.

Authors: Andrew J Kennedy; Alexandra M Bruce; Catherine Gineste; T Eric Ballard; Igor N Olekhnovich; Timothy L Macdonald; Paul S Hoffman
Journal: Antimicrob Agents Chemother Date: 2016-06-20 Impact factor: 5.191

6. Amixicile, a novel inhibitor of pyruvate: ferredoxin oxidoreductase, shows efficacy against Clostridium difficile in a mouse infection model.

Authors: Cirle A Warren; Edward van Opstal; T Eric Ballard; Andrew Kennedy; Xia Wang; Mary Riggins; Igor Olekhnovich; Michelle Warthan; Glynis L Kolling; Richard L Guerrant; Timothy L Macdonald; Paul S Hoffman
Journal: Antimicrob Agents Chemother Date: 2012-05-14 Impact factor: 5.191