Synthesis of a benzomacrolactone-based somatostatin mimetic

Jian Zhou; Marie-Christine Matos; Paul V Murphy

doi:10.1021/ol202528k

Synthesis of a benzomacrolactone-based somatostatin mimetic

Org Lett. 2011 Nov 4;13(21):5716-9. doi: 10.1021/ol202528k. Epub 2011 Oct 11.

Authors

Jian Zhou¹, Marie-Christine Matos, Paul V Murphy

Affiliation

¹ School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland.

PMID: 21988463
DOI: 10.1021/ol202528k

Abstract

The benzomacrolactone is a framework found in numerous natural products. The synthesis of an orthogonally functionalized benzomacrolactone from D-glucosamine and a salicylic acid derivative is described. This macrolactone was used for the synthesis of a somatostatin mimetic that has submicromolar affinity for the human somatostatin receptor 4 (hSSTR4).

Publication types

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

MeSH terms

Benzyl Compounds / chemical synthesis*
Benzyl Compounds / metabolism
Biomimetic Materials / chemical synthesis*
Biomimetic Materials / metabolism
Humans
Lactones / chemical synthesis*
Lactones / metabolism
Molecular Structure
Receptors, Somatostatin / metabolism
Somatostatin / chemistry*
Structure-Activity Relationship

Substances

Benzyl Compounds
Lactones
Receptors, Somatostatin
somatostatin receptor subtype-4
Somatostatin