Preparation of novel 2‐(benzo[<i>b</i>]furan‐2‐yl)‐1<i>H</i>‐imidazolines for photoaffinity labelling and affinity isolation of imidazoline binding

Clews, Proteins J.; Ramsden, Christopher A.; Morgan, Noel G.

doi:10.1002/jhet.5570380237

Cited by 5 publications

(1 citation statement)

References 12 publications

(12 reference statements)

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“…Both in situ imidate formation and isolation of the imidate were investigated under a variety of conditions. No product formation was observed, even under conditions identical to those that give efaroxan 1 from nitrile 19 [13,14]. …”

Section: Methodsmentioning

confidence: 78%

Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands

Farn¹,

Ramsden²,

Morgan³

2008

Journal of Heterocyclic Chem

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The preparation and characterization of new analogues of the imidazoline insulin secretagogue efaroxan 1 are described. These include 1,2,4-triazole, 1,3,4-oxadiazole, pyrimidine, 1,4,5,6-tetrahydropyrimidine and 1,2-dihydro-1,2,4,5-tetrazine analogues. Bromination of 2,3-dihydro-2-ethylbenzo[b]furan-2-carbonitrile 19 gives the 3,3-dibromo analogue 28, which is readily hydrolysed to the corresponding ketone 29. Reduction of this ketone gives the alcohol 31 as a mixture of diastereoisomers that is converted to the fluoride 32 using diethylaminosulfur trifluoride.

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Section: Methodsmentioning

confidence: 78%

Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands

Farn¹,

Ramsden²,

Morgan³

2008

Journal of Heterocyclic Chem

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ChemInform Abstract: Preparation of Novel 2‐(Benzo[b]furan‐2‐yl)‐1H‐imidazolines for Photoaffinity Labeling and Affinity Isolation of Imidazoline Binding Proteins.

2001

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Preparation of Novel 2-(Benzo[b]furan-2-yl)-1H-imidazolines for Photoaffinity Labeling and Affinity Isolation of Imidazoline BindingProteins.-Compounds (VII) and (VIII) retain the capacity to stimulate insulin secretion via the putative I 3 imidazoline receptor and are useful biological tools for affinity chromatography studies and photoaffinity labeling studies of imidazoline binding proteins. -(CLEWS, J.; MORGAN, NOEL G.; RAMSDEN, CHRISTOPHER A.; J. Heterocycl. Chem. 38 (2001) 2, 519-521; Sch. Chem. Phys., Keele Univ., Keele, Staffordshire ST5 5BG, UK; EN)

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Enantioselective synthesis of 2-ethyl-2,3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-efaroxan, from a Baylis–Hillman adduct

Silveira

Coelho

2005

Tetrahedron Letters

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Preparation of novel 2‐(benzo[b]furan‐2‐yl)‐1H‐imidazolines for photoaffinity labelling and affinity isolation of imidazoline binding

Cited by 5 publications

References 12 publications

Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands

Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands

ChemInform Abstract: Preparation of Novel 2‐(Benzo[b]furan‐2‐yl)‐1H‐imidazolines for Photoaffinity Labeling and Affinity Isolation of Imidazoline Binding Proteins.

Enantioselective synthesis of 2-ethyl-2,3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-efaroxan, from a Baylis–Hillman adduct

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