Solid-phase synthesis of cyclic imides

Journal of Combinatorial Chemistry

Volumn 1, Issue 2, 1999, Pages 151-156

  Barn, David R ^a   Richard Morphy, J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IMIDE; PLANT RESIN; POLYSTYRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DESIGN; METHODOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; IMIDES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; POLYSTYRENES; RESINS, PLANT; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033085818     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc980024q     Document Type: Article

References (13)

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2. Kolodziej, S. A.; Hamper B. C. Tetrahedron Lett. 1996, 37, 5277.
3. Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47.
4. Tietze, L. F.; Steinmetz, A. Synlett 1996, 667.
5. The formation of succinimides on a polystyrene resin has been observed as a side reaction during acidic cleavage of peptides containing an Asp-Gly sequence in which the aspartic acid residue is protected with a β-bemyl ester. See Yang, C. C.; Merrifield, R. B. J. Org. Chem. 1976, 41, 1032.
6. This information was obtained by searching the World Drugs Index (Derwent Information Ltd.) for compounds containing substituted succinimide rings, including phthalimides.
7. -1. As the cleavage reaction proceeded, both ester and amide bands diminished in intensity.
8. Ramage, R.; Stewart, A. S. J. J. Chem. Soc., Perkin Trans. 1 1993, 1947.
9. Judging by the intensity of the carbonyl bands in the FT-IR spectra, the coupling and amidation reactions appear to occur equally successfully for the phthalic, succinic, and glutaric systems. However, after the cleavage step (conditions C), whereas the phthalimide carbonyl bands are much reduced in intensity, the intensity of the succinyl bands are only slightly reduced and the glutaryl bands are not reduced at all.
10. 1H NMR spectroscopy.
11. Barnes, R. A.; Godfrey, J. C. J. Org. Chem. 1957, 22, 1043.
12. 3H]-U69593 (0.15 nM) to guinea pig brain membranes.
13. Compounds 9 and 12 were synthesised in two steps (tosylation/Boc protection, followed by dephthaloylation) from 1-(N-phthaloyl-2-aminoethyl)-1,2,3,4-tetrahydroisoquinoline, itself prepared according to the procedure in Biomed. Biochem. Acta 1990, 49 (1), 103-113.