Exploring a pocket for polycycloaliphatic groups in the CXCR3 receptor with the aid of a modular synthetic strategy

Maikel Wijtmans; Dennis Verzijl; Cindy M E van Dam; Leontien Bosch; Martine J Smit; Rob Leurs; Iwan J P de Esch

doi:10.1016/j.bmcl.2009.02.093

Exploring a pocket for polycycloaliphatic groups in the CXCR3 receptor with the aid of a modular synthetic strategy

Bioorg Med Chem Lett. 2009 Apr 15;19(8):2252-7. doi: 10.1016/j.bmcl.2009.02.093. Epub 2009 Feb 27.

Authors

Maikel Wijtmans¹, Dennis Verzijl, Cindy M E van Dam, Leontien Bosch, Martine J Smit, Rob Leurs, Iwan J P de Esch

Affiliation

¹ Division of Medicinal Chemistry, Faculty of Sciences, Leiden/Amsterdam Center for Drug Research, VU University Amsterdam, Amsterdam, The Netherlands.

PMID: 19299127
DOI: 10.1016/j.bmcl.2009.02.093

Abstract

A CXCR3 pocket capable of accommodating polycycloaliphatics was explored using a modular synthetic strategy. The systematic studies reveal that the tricyclic 2-adamantane and bicyclic (iso)bornyl group are efficiently recognized by CXCR3.

Publication types

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

MeSH terms

Adamantane / chemistry
Amination
Binding Sites / physiology
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
Camphanes / chemistry
Cell Line
Humans
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / metabolism*
Receptors, CXCR3 / chemistry
Receptors, CXCR3 / metabolism*
Structure-Activity Relationship

Substances

Bridged Bicyclo Compounds, Heterocyclic
CXCR3 protein, human
Camphanes
Polycyclic Compounds
Receptors, CXCR3
camphane
Adamantane