Synthesis of somatostatin mimetics based on 1-deoxynojirimycin

ChemMedChem
Vincent ChagnaultPaul V Murphy

Abstract

The synthesis of novel somatostatin mimetics from 1-deoxynojirimycin (DNJ) is described. The dipeptide mimetic, which respectively displayed the side chains of tryptophan and lysine at the nitrogen and O6 atoms of the iminosugar scaffold is a ligand (K(i)=3.2 microM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (K(i)>100 microM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (K(i)=5 microM).

References

May 1, 1993·Proceedings of the National Academy of Sciences of the United States of America·L RohrerR Schüle
Mar 1, 1997·Bioorganic & Medicinal Chemistry·Y Le MerrerM J Foglietti
Jun 9, 1999·Current Opinion in Chemical Biology·F Schweizer, O Hindsgaul
Aug 28, 1999·Journal of Medicinal Chemistry·M J SofiaH R Axelrod
Dec 11, 1999·Nucleic Acids Research·H M BermanP E Bourne
Feb 14, 2002·Chemical Reviews·Sibylle A W GrunerHorst Kessler
Apr 12, 2002·Current Medicinal Chemistry·Tushar K ChakrabortySarva Jayaprakash
May 23, 2002·Current Opinion in Chemical Biology·Lisa A Marcaurelle, Peter H Seeberger
May 11, 2004·The Journal of Organic Chemistry·Ciaran McDonnellPaul V Murphy
Mar 31, 2005·Chemistry : a European Journal·Daniel B Werz, Peter H Seeberger
Jun 2, 2005·Biopolymers·Knud J Jensen, Jesper Brask
Oct 8, 2005·The Journal of Organic Chemistry·Sebastien G Gouin, Paul V Murphy
Aug 22, 2006·Current Medicinal Chemistry·Luca GentilucciFederico Squassabia
Sep 20, 2006·ChemMedChem·Wim MeutermansBernd Becker
Dec 16, 2006·Mini Reviews in Medicinal Chemistry·Bernd BeckerWim Meutermans
Oct 2, 1998·Angewandte Chemie·Tobias WunbergHorst Kunz

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Citations

Aug 20, 2014·Proceedings of the National Academy of Sciences of the United States of America·Ana CuervoLaura Fumagalli
Oct 13, 2011·Organic Letters·Jian ZhouPaul V Murphy
Jan 5, 2011·Bioorganic & Medicinal Chemistry Letters·Yunxue ZhaoPaul V Murphy
Oct 11, 2014·Angewandte Chemie·Zhaohong LuAng Li
Dec 5, 2018·European Journal of Medicinal Chemistry·Arvind NegiPaul V Murphy
Aug 5, 2008·Organic Letters·Ying Zhou, Paul V Murphy
Oct 30, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Debashis DharaPaul V Murphy

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