The solid phase synthesis of a series of tri-substituted hydantoin ligands for the somatostatin SST5 receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 24, 1998, Pages 3609-3614

  Sciciński, Jan J ^a   Barker, Michael D ^b   Murray, Peter John ^a   Jarvie, Emma M ^c  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b Cell Biology Unit   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AF 15831; BIM 23027; HYDANTOIN DERIVATIVE; OCTREOTIDE; RECEPTOR SUBTYPE; SOMATOSTATIN RECEPTOR; SOMATOSTATIN RECEPTOR STIMULATING AGENT; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG BIOAVAILABILITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; HORMONE PROTEIN COMPLEX; HORMONE RECEPTOR INTERACTION; LIGAND BINDING; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS;

ANIMALS; CHO CELLS; CRICETINAE; HUMANS; HYDANTOINS; IODINE RADIOISOTOPES; LIGANDS; RADIOLIGAND ASSAY; RECEPTORS, SOMATOSTATIN; RECOMBINANT PROTEINS; SOMATOSTATIN;

EID: 0032535564     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00647-7     Document Type: Article

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28. 28. Typical procedure: To a suspension of the resin 6 (approx. 50 mg) in a 1.8 M solution of the alcohol (10 equiv.) in DCM was added a 1.8 M solution of triphenylphosphine (10 equiv.) in DCM followed by a 1.8M solution of TMAD (10 equiv.) in DCM. After agitating for 17 h the resin was washed successively with DMF, THF and DCM to give the product resin 7 which was agitated with the supernatant (1.5 mL) of a preformed suspension of potassium carbonate (3.4 g) and thiophenol (420 μL) in DMF (40 mL) for 16 h then washed in turn with DMF, THF and DCM to give the secondary amine resin 8.
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30. 30. Typical procedure: The resin 8 (approx. 50 mg) was suspended in a 0.44 M solution of pyridine in DCM (10 equiv.) then treated with a 0.15 M solution of triphosgene in DCM (3 equiv.) and agitated for 3 h then washed with DCM. The resin was resuspended in a 0.44 M solution of pyridine (10 equiv.) then treated with 2-aminoethylpyrrolidine (10 equiv.), agitated for 17 h the drained and washed with DCM. The combined filtrates were evaporated to give the required product hydantoins 4.