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Literature DB >> 21874155

Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis.

Stephen D Lotesta¹, Junjia Liu, Emma V Yates, Inna Krieger, James C Sacchettini, Joel S Freundlich, Erik J Sorensen.

Abstract

New pleuromutilin-like compounds were synthesized in approximately 11 steps from 3-allylcyclopent-2-enone by a strategy featuring sequential carbonyl addition reactions. Several analogs possessing the C14 tiamulin ester side chain displayed activity in a Mycobacterium tuberculosis mc(2)7000 assay. The results described herein provide a basis for further efforts to expand the structural and stereochemical diversity of the pleuromutilin class of bacterial protein synthesis inhibitors through advances in chemical synthesis.

Entities: Chemical Disease Species

Year: 2011 PMID： 21874155 PMCID： PMC3160647 DOI： 10.1039/C1SC00116G

Source DB: PubMed Journal: Chem Sci ISSN： 2041-6520 Impact factor: 9.825

20 in total

1. A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics.

Authors: Mark G Charest; Christian D Lerner; Jason D Brubaker; Dionicio R Siegel; Andrew G Myers
Journal: Science Date: 2005-04-15 Impact factor: 47.728

2. Cyclopentanone ring-cleaved pleuromutilin derivatives.

Authors: Dane M Springer; Amy Bunker; Bing-Yu Luh; Margaret E Sorenson; Jason T Goodrich; Joanne J Bronson; Kenneth DenBleyker; Thomas J Dougherty; Joan Fung-Tomc
Journal: Eur J Med Chem Date: 2006-12-06 Impact factor: 6.514

Review 3. Drugs versus bugs: in pursuit of the persistent predator Mycobacterium tuberculosis.

Authors: James C Sacchettini; Eric J Rubin; Joel S Freundlich
Journal: Nat Rev Microbiol Date: 2008-01 Impact factor: 60.633

4. The bacteria fight back.

Authors: Gary Taubes
Journal: Science Date: 2008-07-18 Impact factor: 47.728

Review 5. Mutilins derivatives: from veterinary to human-used antibiotics.

Authors: Changhua Hu; Yi Zou
Journal: Mini Rev Med Chem Date: 2009-10 Impact factor: 3.862

6. A dialdehyde cyclization cascade: an approach to pleuromutilin.

Authors: Matthew D Helm; Madeleine Da Silva; David Sucunza; Thomas J K Findley; David J Procter
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. Mycobacterium tuberculosis DeltaRD1 DeltapanCD: a safe and limited replicating mutant strain that protects immunocompetent and immunocompromised mice against experimental tuberculosis.

Authors: Vasan K Sambandamurthy; Steven C Derrick; Tsungda Hsu; Bing Chen; Michelle H Larsen; Kripa V Jalapathy; Mei Chen; John Kim; Steven A Porcelli; John Chan; Sheldon L Morris; William R Jacobs
Journal: Vaccine Date: 2006-06-12 Impact factor: 3.641

Review 8. Antibiotics for emerging pathogens.

Authors: Michael A Fischbach; Christopher T Walsh
Journal: Science Date: 2009-08-28 Impact factor: 47.728

9. Fe/Cr- and Co/Cr-mediated catalytic asymmetric 2-haloallylations of aldehydes.

Authors: Michio Kurosu; Mei-Huey Lin; Yoshito Kishi
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

10. New pleuromutilin derivatives with enhanced antimicrobial activity.II.Structure-activity correlations.

Authors: H Egger; H Reinshagen
Journal: J Antibiot (Tokyo) Date: 1976-09 Impact factor: 2.649

10 in total

1. Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

Authors: Junjia Liu; Maurice A Marsini; T Aaron Bedell; Paul J Reider; Erik J Sorensen
Journal: Tetrahedron Date: 2016-03-15 Impact factor: 2.457

10. Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors: Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal: Chemistry Date: 2015-11-26 Impact factor: 5.236

10 in total

Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis.

1. A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics.

2. Cyclopentanone ring-cleaved pleuromutilin derivatives.

Review 3. Drugs versus bugs: in pursuit of the persistent predator Mycobacterium tuberculosis.

4. The bacteria fight back.

Review 5. Mutilins derivatives: from veterinary to human-used antibiotics.

6. A dialdehyde cyclization cascade: an approach to pleuromutilin.

7. Mycobacterium tuberculosis DeltaRD1 DeltapanCD: a safe and limited replicating mutant strain that protects immunocompetent and immunocompromised mice against experimental tuberculosis.

Review 8. Antibiotics for emerging pathogens.

9. Fe/Cr- and Co/Cr-mediated catalytic asymmetric 2-haloallylations of aldehydes.

10. New pleuromutilin derivatives with enhanced antimicrobial activity.II.Structure-activity correlations.

1. Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions.

2. Total Synthesis of (+)-Pleuromutilin.

3. Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

4. A modular and enantioselective synthesis of the pleuromutilin antibiotics.

5. Total synthesis of structurally diverse pleuromutilin antibiotics.

Review 6. The evolving role of chemical synthesis in antibacterial drug discovery.

7. Scalable Synthesis of a Key Intermediate for the Production of Pleuromutilin-Based Antibiotics.

8. Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

9. An antimycobacterial pleuromutilin analogue effective against dormant bacilli.

10. Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.