Second generation analogs of rigid 6,7-spiro scaffolds targeting the bacterial ribosome

Christos I Stathakis; Ioannis Mavridis; Georgia Kythreoti; Athanasios Papakyriakou; Ioannis A Katsoulis; Thomas Cottin; Panoula Anastasopoulou; Dionisios Vourloumis

doi:10.1016/j.bmcl.2010.10.001

Second generation analogs of rigid 6,7-spiro scaffolds targeting the bacterial ribosome

Bioorg Med Chem Lett. 2010 Dec 15;20(24):7488-92. doi: 10.1016/j.bmcl.2010.10.001. Epub 2010 Oct 8.

Authors

Christos I Stathakis¹, Ioannis Mavridis, Georgia Kythreoti, Athanasios Papakyriakou, Ioannis A Katsoulis, Thomas Cottin, Panoula Anastasopoulou, Dionisios Vourloumis

Affiliation

¹ Laboratory of Chemical Biology of Natural Products and Designed Molecules, Institute of Physical Chemistry, NCSR DEMOKRITOS, Athens, Greece.

PMID: 21041083
DOI: 10.1016/j.bmcl.2010.10.001

Abstract

Previous work from our group described the synthesis and biological evaluation of new rigid, 6,6- and 6,7-spiro aminoglycosidic scaffolds targeting the bacterial ribosome. Herein we describe an improved synthetic protocol for their construction, and extend our study by further amino-functionalization of their 6,7-spiro analogs. The synthetic strategy, preparation and evaluation of some representative examples are reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aminoglycosides / chemistry
Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / pharmacology
Bacteria / genetics*
Binding Sites
Computer Simulation
RNA, Ribosomal, 16S / chemistry*
RNA, Ribosomal, 16S / metabolism
Spiro Compounds / chemical synthesis
Spiro Compounds / chemistry*
Spiro Compounds / pharmacology

Substances

Aminoglycosides
Anti-Bacterial Agents
RNA, Ribosomal, 16S
Spiro Compounds