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Volumn 64, Issue 5, 1999, Pages 1723-1726

Solid-phase synthesis of BRL 49653

Author keywords

[No Author keywords available]

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; CLOFIBRATE; DRUG DERIVATIVE; ISOPROTEIN; LINOLEIC ACID; PEROXISOME PROLIFERATOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; PROSTAGLANDIN; ROSIGLITAZONE;

EID: 0033525496     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981931k     Document Type: Note
Times cited : (22)

References (22)
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    • This work was first presented at the 215th National Meeting of the American Chemical Society, Dallas, Texas, April, 1998. During our investigation toward the preparation of BRL 49653 on the solid support, another study involving the preparation of a library of thiazolidinedione - fatty acid PPARγ ligands was reported. This approach assembled subunits A, B, and C, using standard solution-phase techniques, and then attached the functionalized thiazolidinedione to a 2-chlorotrityl chloride resin. This functionalized thiazolidinedione (TZD) was then diversified on the support by coupling the supported TZD with a variety of straight-chain alkyl-and alkenyl-carboxylic acids. Tomkinson, N. C. O.; Sefler, A. M.; Plunket, K. D.; Blanchard, S. G.; Parks, D. J.; Willson, T. M. Bioorg. Med. Chem. Lett. 1997, 7, 2491. In addition, the polymer-supported synthesis of 4-thiazolidinones derived from amino acids has been reported, and a library of analogues have been prepared. Holmes, C. P.; Chinn, J. P.; Look, G. C.; Gordon E. M.; Gallop, M. A. J. Org. Chem. 1995, 60, 7328.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 2491
    • Tomkinson, N.C.O.1    Sefler, A.M.2    Plunket, K.D.3    Blanchard, S.G.4    Parks, D.J.5    Willson, T.M.6
  • 9
    • 0000058677 scopus 로고
    • This work was first presented at the 215th National Meeting of the American Chemical Society, Dallas, Texas, April, 1998. During our investigation toward the preparation of BRL 49653 on the solid support, another study involving the preparation of a library of thiazolidinedione - fatty acid PPARγ ligands was reported. This approach assembled subunits A, B, and C, using standard solution-phase techniques, and then attached the functionalized thiazolidinedione to a 2-chlorotrityl chloride resin. This functionalized thiazolidinedione (TZD) was then diversified on the support by coupling the supported TZD with a variety of straight-chain alkyl-and alkenyl-carboxylic acids. Tomkinson, N. C. O.; Sefler, A. M.; Plunket, K. D.; Blanchard, S. G.; Parks, D. J.; Willson, T. M. Bioorg. Med. Chem. Lett. 1997, 7, 2491. In addition, the polymer-supported synthesis of 4-thiazolidinones derived from amino acids has been reported, and a library of analogues have been prepared. Holmes, C. P.; Chinn, J. P.; Look, G. C.; Gordon E. M.; Gallop, M. A. J. Org. Chem. 1995, 60, 7328.
    • (1995) J. Org. Chem. , vol.60 , pp. 7328
    • Holmes, C.P.1    Chinn, J.P.2    Look, G.C.3    Gordon, E.M.4    Gallop, M.A.5
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    • Albericio, F.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. J. Org. Chem. 1990, 55, 3730. Landi, J. J., Jr.; Ramig, K. Synth. Commun. 1991, 21, 167. Carvalho, C. F.; Sargent, M. V. J. Chem. Soc., Perkin Trans. 1 1984, 1605.
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    • For preparation, see: Castro, J. L.; Matassa, V. G.; Ball, R. G. J. Org. Chem. 1994, 59, 2289. For application in SPOC, see: Swayze, E. E. Tetrahedron Lett. 1997, 38, 8465.
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    • note
    • Lower chemical yields were obtained as a result of the formation of significant amounts of byproducts resulting from the coupling reaction between the substrate and DEAD.
  • 19
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    • Bolton, G. L. Tetrahedron Lett. 1997, 53, 6611. Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. Brestensky, D. M.; Huseland, D. E.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1988, 29, 3749. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
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    • Bolton, G. L. Tetrahedron Lett. 1997, 53, 6611. Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. Brestensky, D. M.; Huseland, D. E.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1988, 29, 3749. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
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    • Bolton, G. L. Tetrahedron Lett. 1997, 53, 6611. Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237. Brestensky, D. M.; Huseland, D. E.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1988, 29, 3749. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.