Synthesis and antibacterial activity of [6,5,5] and [6,6,5] tricyclic fused oxazolidinones

D M Gleave; S J Brickner; P R Manninen; D A Allwine; K D Lovasz; D C Rohrer; J A Tucker; G E Zurenko; C W Ford

doi:10.1016/s0960-894x(98)00194-2

Synthesis and antibacterial activity of [6,5,5] and [6,6,5] tricyclic fused oxazolidinones

Bioorg Med Chem Lett. 1998 May 19;8(10):1231-6. doi: 10.1016/s0960-894x(98)00194-2.

Authors

D M Gleave¹, S J Brickner, P R Manninen, D A Allwine, K D Lovasz, D C Rohrer, J A Tucker, G E Zurenko, C W Ford

Affiliation

¹ Pharmacia & Upjohn, Kalamazoo, MI 49001, USA.

PMID: 9871741
DOI: 10.1016/s0960-894x(98)00194-2

Abstract

A series of conformationally restricted, [6,5,5] and [6,6,5] tricyclic fused oxazolidinones were synthesized and tested for antibacterial activity. Several compounds in the trans-[6,5,5] series demonstrated potent in vitro and in vivo activity. This work provides valuable information regarding the preferred conformational orientation of the oxazolidinones at the binding site.

MeSH terms

Animals
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology
Bacteria / drug effects*
Bacterial Infections / drug therapy*
Indicators and Reagents
Mice
Microbial Sensitivity Tests
Models, Molecular
Molecular Conformation
Molecular Structure
Oxazoles / chemical synthesis*
Oxazoles / chemistry
Oxazoles / pharmacology
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Indicators and Reagents
Oxazoles