Photochemical rearrangement of oxaziridines and nitrones in the hexahydroindole series: a convenient synthetic route to 1-azabicyclo[5.2.0]nonan-2-ones as novel RGD mimetics

E Bourguet; J L Baneres; J P Girard; J Parello; J P Vidal; X Lusinchi; J P Declercq

doi:10.1021/ol016184j

Photochemical rearrangement of oxaziridines and nitrones in the hexahydroindole series: a convenient synthetic route to 1-azabicyclo[5.2.0]nonan-2-ones as novel RGD mimetics

Org Lett. 2001 Oct 4;3(20):3067-70. doi: 10.1021/ol016184j.

Authors

E Bourguet¹, J L Baneres, J P Girard, J Parello, J P Vidal, X Lusinchi, J P Declercq

Affiliation

¹ Laboratoire de Chimie Biomoléculaire et Interactions Biologiques, UMR CNRS 5074, Faculté de Pharmacie, 15, avenue Charles Flahault, 34060 Montpellier Cedex, France.

PMID: 11573996
DOI: 10.1021/ol016184j

Abstract

[reaction: see text] Photolysis of oxaziridines a or nitrones b provides a convenient synthetic route to fused bicyclic lactams c adequately substituted on both cycles A and B as scaffolds for mimicking conformationally constrained beta-turn peptides as in the tripeptide RGD signaling motif of fibronectin.

Publication types

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

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Crystallography, X-Ray
Indoles / chemistry*
Lactams / chemical synthesis*
Molecular Mimicry
Molecular Structure
Nitrogen Oxides / chemistry*
Oligopeptides / chemistry*
Photochemistry

Substances

Bridged Bicyclo Compounds
Indoles
Lactams
Nitrogen Oxides
Oligopeptides
nitrones
arginyl-glycyl-aspartic acid