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

The strategic use of specific polycycloaliphatic groups in obtaining small antagonists for the CXCR3 receptor was investigated. 2-Adamantyl- and (iso)bornyl groups proved beneficial. A CXCR3 pocket capable of accommodating polycycloaliphatics was explored using a modular synthetic strategy. The syst...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2009-04, Vol.19 (8), p.2252-2257
Main Authors: Wijtmans, Maikel, Verzijl, Dennis, van Dam, Cindy M.E., Bosch, Leontien, Smit, Martine J., Leurs, Rob, de Esch, Iwan J.P.
Format: Article
Language:English
Subjects:
Adamantane - chemistry
Amination
Binding Sites - physiology
Biological and medical sciences
Bornanes - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Cell Line
CXCR3
GPCR
Humans
Medical sciences
Miscellaneous
Pharmacology. Drug treatments
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - metabolism
Polycycloaliphatic
Receptors, CXCR3 - chemistry
Receptors, CXCR3 - metabolism
Reductive amination
Structure-Activity Relationship
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Summary:The strategic use of specific polycycloaliphatic groups in obtaining small antagonists for the CXCR3 receptor was investigated. 2-Adamantyl- and (iso)bornyl groups proved beneficial. 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2009.02.093