Fluoroalkyl alpha side chain containing 3,4-diamino-cyclobutenediones as potent and orally bioavailable CXCR2-CXCR1 dual antagonists

Purakkattle Biju; Arthur G Taveras; Michael P Dwyer; Younong Yu; Jianhua Chao; R William Hipkin; Xuedong Fan; Diane Rindgen; Jay Fine; Daniel Lundell

doi:10.1016/j.bmcl.2009.01.033

Fluoroalkyl alpha side chain containing 3,4-diamino-cyclobutenediones as potent and orally bioavailable CXCR2-CXCR1 dual antagonists

Bioorg Med Chem Lett. 2009 Mar 1;19(5):1431-3. doi: 10.1016/j.bmcl.2009.01.033. Epub 2009 Jan 15.

Authors

Purakkattle Biju¹, Arthur G Taveras, Michael P Dwyer, Younong Yu, Jianhua Chao, R William Hipkin, Xuedong Fan, Diane Rindgen, Jay Fine, Daniel Lundell

Affiliation

¹ Schering-Plough Research Institute, Kenilworth, NJ 07033, USA.

PMID: 19196511
DOI: 10.1016/j.bmcl.2009.01.033

Abstract

A series of potent and orally bioavailable 3,4-diaminocyclobutenediones with various fluoroalkyl groups as alpha side chain were prepared and found to show significant improvements in the binding affinities towards both CXCR2 and CXCR1 receptors.

Publication types

Comparative Study

MeSH terms

Administration, Oral
Animals
Binding Sites
Cyclobutanes / administration & dosage
Cyclobutanes / chemical synthesis*
Cyclobutanes / metabolism
Protein Binding
Rats
Receptors, Interleukin-8A / antagonists & inhibitors*
Receptors, Interleukin-8A / metabolism
Receptors, Interleukin-8B / antagonists & inhibitors*
Receptors, Interleukin-8B / metabolism

Substances

Cyclobutanes
Receptors, Interleukin-8A
Receptors, Interleukin-8B