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Eur J Med Chem. 2016 May 23;114:59-64. doi: 10.1016/j.ejmech.2016.02.046. Epub 2016 Feb 21.

Chroman-4-one and chromone based somatostatin β-turn mimetics.

Author information

1
Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
2
Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden; Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki, FIN-00014, Helsinki, Finland.
3
Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden. Electronic address: luthman@chem.gu.se.

Abstract

A scaffold approach has been used to develop somatostatin β-turn mimetics based on chroman-4-one and chromone ring systems. Such derivatives could adopt conformations resembling type II or type II' β-turns. Side chain equivalents of the crucial Trp8 and Lys9 in somatostatin were introduced in the 2- and 8-positions of the scaffolds using efficient reactions. Interestingly, this proof-of-concept study shows that 4 and 9 have Ki-values in the low μM range when evaluated for their affinity for the sst2 and sst4 receptors.

KEYWORDS:

Chroman-4-one; Chromone; Peptidomimetics; Somatostatin

PMID:
26974375
DOI:
10.1016/j.ejmech.2016.02.046
[Indexed for MEDLINE]

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