What question did this study set out to answer?

To design and synthesize conformationally constrained tricyclic analogues of linezolid to explore structure-activity relationships and improve antibacterial potency against Gram-positive organisms.

August 1, 2002Journal of Medicinal Chemistry

Synthesis of Conformationally Constrained Analogues of Linezolid: Structure−Activity Relationship (SAR) Studies on Selected Novel Tricyclic Oxazolidinones

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To design and synthesize conformationally constrained tricyclic analogues of linezolid to explore structure-activity relationships and improve antibacterial potency against Gram-positive organisms.
Designed and synthesized novel tricyclic oxazolidinone scaffolds mimicking the entropic bioactive conformation of linezolid.
Incorporated fluorine into the aromatic core and systematically substituted the amide functionality with diverse homologues, thioamides, thiocarbamates, and thioureas.
Screened all synthesized analogues in vitro to evaluate antibacterial activity against a panel of Gram-positive organisms.
Introduction of a fluorine atom into the tricyclic core significantly enhanced antibacterial activity against Gram-positive organisms, identifying lead compound 16.
Aliphatic amide homologues (compounds 25–30) maintained antibacterial potency with up to four carbon atoms positioned on the amide nitrogen.
Thioamide and thiocarbamate derivatives displayed markedly greater antibacterial potency relative to their corresponding amide and carbamate analogues.

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Implication

In vitro study demonstrates potent antibacterial efficacy of tricyclic oxazolidinones against Gram-positive bacteria, highlighting a promising structural strategy for new antibiotics.

Cite This Study

Selvakumar et al. (2002) studied this question.

synapsesocial.com/papers/6ab4a622681f7b53e3fd7e06 https://doi.org/10.1021/jm020092y

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Implication

In vitro study demonstrates potent antibacterial efficacy of tricyclic oxazolidinones against Gram-positive bacteria, highlighting a promising structural strategy for new antibiotics.

Synthesis of Conformationally Constrained Analogues of Linezolid: Structure−Activity Relationship (SAR) Studies on Selected Novel Tricyclic Oxazolidinones

Key Points

Discussion

Implication

Cite This Study

Synthesis of Conformationally Constrained Analogues of Linezolid: Structure−Activity Relationship (SAR) Studies on Selected Novel Tricyclic Oxazolidinones

Key Points

Discussion

Implication

Cite This Study

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