Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A.

doi:10.1021/JM0400810

Paper

Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A.

Published Jan 4, 2005 · F. Reck, Feiyu Zhou, Marc Girardot

Journal of medicinal chemistry

Q1 SJR score

242

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Oxazolidinones represent a new and promising class of antibacterial agents. Current research in this area is mainly concentrated on improving the safety profile and the antibacterial spectrum. Many oxazolidinones, including linezolid (marketed as Zyvox), are inhibitors of monoamine oxidase A (MAO-A), which presents an undesired side effect. Recently, it was found that the 1,2,3-triazole is a good replacement for the conventional acetamide functionality found in oxazolidinones. We now disclose the finding that 1,2,3-triazoles bearing a substituent like methyl, small substituted methyl, bromo, or a linear (sp-hybridized) group at the 4 position (compounds such as 5, 16, 19, and 21) are good antibacterials with reduced or no activity, within the detection limit of the assay, against MAO-A. The results are especially promising for the development of oxazolidinones with an improved safety profile. The MAO-A SAR can be rationalized on the basis of docking studies to a MAO-A/MAO-B homology model.

Highly Cited

Study Snapshot

4-substituted 1,2,3-triazoles show potential as antibacterial agents with reduced activity against monoamine oxidase A, offering an improved safety profile for oxazolidinones.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Identification of 4-substituted 1,2,3-triazoles as novel oxazolidinone antibacterial agents with reduced activity against monoamine oxidase A.

Sign up to use Study Snapshot

References

Citations

Pd-Catalyzed/Ligand-Controlled Regioselective Asymmetric Hydrosulfonylation of Alkylallenes or Arylallenes.

This study demonstrates a palladium-catalyzed/ligand-controlled asymmetric hydrosulfonylation of alkylallenes and arylallenes, resulting in high yields and enantioselectivities up to 90% and 99%, for the construction of

Convergent synthesis, kinetics and computational attributions of indole-N-phenyltriazole hybrids bearing N-(aryl)butanamides as alkaline phosphatase inhibitors

These indole-N-phenyltriazole hybrids bearing N-(aryl)butanamides show promising inhibitory activity against alkaline phosphatase, potentially aiding in normal bone and tooth calcification.

Synthesis of γ-keto sulfones through sulfonylation/acylation of alkenes merging NHC- and photo-catalysis

This study developed a three-component coupling of alkenes, sodium sulfinates, and acyl imidazoles to synthesize -keto sulfones with good functional group tolerance using NHC/photocatalysis and a rare radical/radical

Structural toxicity relationship (STR) of linezolid to mitigate myelosuppression and serotonergic toxicity.

Modifications to Linezolid's structure could lead to safer derivatives with reduced myelosuppression and MAO inhibition, improving their therapeutic profiles for combating drug-resistant TB.

Recent advances in triazole synthesis via click chemistry and their pharmacological applications: A review.

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry has advanced in synthesizing biologically important triazole molecules, aiding in drug discovery and optimization processes.

Pd-Catalyzed Aerobic Synthesis of Allylic Sulfones from Allylic Alcohols and Sulfonyl Hydrazines in Water.

Pd-catalyzed aerobic synthesis of allylic sulfones from allylic alcohols and sulfonyl hydrazines in water is a mild, green, and practical method that can be scaled up in gram scale.