Natural products in parallel synthesis: Triazole libraries of nonactic acid

Luesse, Sarah B.; Wells, Gregg B.; Nayek, Abhijit; Smith, Anne M.; Kusche, Brian R.; Bergmeier, Stephen C.; McMills, Mark C.; Priestley, Nigel D.; Wright, Dennis L.

doi:10.1016/j.bmcl.2008.06.020

Cited by 12 publications

(7 citation statements)

References 19 publications

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“…The synthesis of a library of nonactic acid‐derived triazoloamide derivatives ( 56 ) and their evaluation as antimicrobial agents was described by Luesse et al 120…”

Section: Click Reactions and The Pharmacological Applications Of 1supporting

confidence: 81%

“…The synthesis of a library of nonactic acid-derived triazoloamide derivatives (56) and their evaluation as antimicrobial agents was described by Luesse et al [120] Sumangala and co-workers synthesized a 1,2,3-triazolecontaining quinoline moiety (57). [121] They studied their antimicrobial and antifungal activity by using cyclo-piroxolamine as standard antifungal agent.…”

Section: Antifungal and Antibacterialsmentioning

confidence: 99%

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Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,155

508

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The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of click chemistry due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.

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“…The synthesis of a library of nonactic acid‐derived triazoloamide derivatives ( 56 ) and their evaluation as antimicrobial agents was described by Luesse et al 120…”

Section: Click Reactions and The Pharmacological Applications Of 1supporting

confidence: 81%

Section: Antifungal and Antibacterialsmentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,155

508

View full text Add to dashboard Cite

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“…[18,19] The discovered instability of compound 24 presents a concern that the shelf life of such conjugates can be affected. To further investigate this phenomenon, we hypothesized that the basicity of the adjacent triazole ring is responsible for intramolecular acceleration of carbamate hydrolysis.…”

Section: Communicationmentioning

confidence: 99%

“Double‐Click” Protocol for Synthesis of Heterobifunctional Multivalent Ligands: Toward a Focused Library of Specific Norovirus Inhibitors

Guiard

Fiege

Kitov

et al. 2011

Chemistry A European J

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“…10 Our aim has been to modify polyketide biosynthesis to make downstream synthetic manipulations easier rather than to generate new compounds directly. We recognized at an early stage that our experience in the biosynthesis of the macrotetrolide antibiotic nonactin would make this an ideal model system.…”

mentioning

confidence: 99%

“…12 Nonactic acid is an outstanding natural product scaffold for library development. 10 The C-8 alcohol and C-1 carboxyl groups can be readily diversified with little requirement for protecting group manipulations. The central core of the scaffold is available in both enantiomeric series allowing for the straightforward introduction of stereochemical diversity into a library of compounds.…”

mentioning

confidence: 99%

Natural product derivatives with bactericidal activity against Gram-positive pathogens including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecalis

Phillips

Smith

Kusche

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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We have shown that the intentional engineering of a natural product biosynthesis pathway is a useful way to generate stereochemically complex scaffolds for use in the generation of combinatorial libraries that capture the structural features of both natural products and synthetic compounds. Analysis of a prototype library based upon nonactic acid lead to the discovery of triazole-containing nonactic acid analogs, a new structural class of antibiotic that exhibits bactericidal activity against drug resistant, Gram-positive pathogens including Staphylococcus aureus and Enterococcus faecalis.

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Natural products in parallel synthesis: Triazole libraries of nonactic acid

Cited by 12 publications

References 19 publications

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

“Double‐Click” Protocol for Synthesis of Heterobifunctional Multivalent Ligands: Toward a Focused Library of Specific Norovirus Inhibitors

Natural product derivatives with bactericidal activity against Gram-positive pathogens including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecalis

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