Synthesis and TNF expression inhibitory properties of new thalidomide analogues derived via Heck cross coupling

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 21, 2007, Pages 5819-5824

  Stewart, Scott G ^a   Spagnolo, Daniel ^a   Polomska, Marta E ^a   Sin, Melvin ^a   Karimi, Mahdad ^b   Abraham, Lawrence J ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

Cross coupling reaction; Heck reaction; Phthalimide; Thalidomide; TNF reporter; Tumour necrosis factor (TNF)

Indexed keywords

3 (4 AMINO 1,3 DIHYDRO 1,3 DIOXO 2H ISOINDOL 2 YL)GLUTARIMIDE; ANDROGEN RECEPTOR; BASIC FIBROBLAST GROWTH FACTOR; CYTOKINE; I KAPPA B KINASE ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; IMMUNOMODULATING AGENT; LENALIDOMIDE; PHTHALIMIDE DERIVATIVE; PROSTAGLANDIN SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; THALIDOMIDE; THALIDOMIDE DERIVATIVE; TUMOR NECROSIS FACTOR;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; GENETIC TRANSCRIPTION; HECK REACTION; HUMAN; HUMAN CELL; IMMUNOMODULATION; LEUKEMIA CELL LINE; PROMOTER REGION; RECEPTOR BLOCKING;

HUMANS; JURKAT CELLS; THALIDOMIDE; TUMOR NECROSIS FACTOR-ALPHA;

EID: 34548849135     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.08.042     Document Type: Article

References (34)

1. Brynner, R.; Stephens. T. Dark Remedy, The impact of thalidomide and its revival as a vital medicine, 2001, Perseus.
2. Ribatti D., and Vacca A. Leukemia 19 (2005) 1525
3. Bartlett J.B., Dredge K., and Dalgleish A.G. Nature Rev. 4 (2004) 314
4. Sheskin J. Clin. Pharmacol. Ther. 6 (1962) 303
5. Celgene global pharmaceutical company, , has remarketed thalidomide (thalomid™) as immunomodulatory drug (IMiD™).
6. Gutierrez-Rodriguez O. Arthritis Rheum. 27 (1984) 1118
7. Hamza M.H. Clin. Rheumatol. 5 (1986) 365
8. Franks M.E., Macpherson G.R., and Figg W.D. Lancet 363 (2004) 1802
9. Baas P., Boogerd W., Dalesio O., Haringhuzen A., Custers F., and van Zandwijk N. Lung Cancer 48 (2005) 291
10. Sano H., Noguchi T., Tanatani A., Hashimoto Y., and Miyachi H. Bioorg. Med. Chem. Lett. 15 (2005) 3079
11. Keifer J., Guttridge D.C., Ashburner B.P., and Baldwin A.S. J. Biol. Chem. 276 (2001) 22382
12. Périno S., Contino-Pépin C., Satchi-Fainaro R., Butterfield C., and Pucci B. Bioorg. Med. Chem. Lett. 14 (2004) 421
13. Nakamura T., Noguchi T., Kobayashi H., Miyachi H., and Hashimoto Y. Chem. Pharm. Bull. 54 (2006) 1709
14. Muller G.W., Chen R., Huang S.-Y., Corral L.G., Wong L.W., Patterson R.T., Chen Y., Kaplan G., and Stirling D.I. Bioorg. Med. Chem. Lett. 9 (1999) 1625
15. Miyachi H., Ogasawara A., Azuma A., and Hashimoto Y. Bioorg. Med. Chem. 5 (1997) 2095
16. Machado A.L., Lima L.M., Araújo J.X., Fraga C.A.M., Koatz V.L.G., and Barreiro E.J. Bioorg. Med. Chem. Lett. 15 (2005) 1169
17. Inatsuki S., Noguchi T., Miyachi H., Oda S., Iguchi T., Kizaki M., Hashimoto Y., and Kobayashi H. Bioorg. Med. Chem. Lett. 15 (2005) 321
18. Alonso F., Beletskaya I.P., and Yus M. Tetrahedron 61 (2005) 11771
19. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
20. Tietze L.F., Stewart S.G., Polomska M.E., Modi A., and Zeeck A. Chem. Eur. J. 10 (2004) 5233
21. Tietze L.F., Stewart S.G., and Polomska M.E. Eur. J. Org. Chem. (2005) 1752
22. Littke A.F., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 6989
23. Nicolaou K.C., Bulger P.G., and Saralah D. Angew. Chem. Int. Ed. 44 (2005) 4442
24. Muller G.W., Konnecke W.E., Smith A.M., and Khetani V.D. Org. Process Res. Dev. 3 (1999) 139
25. Capitosti S.M., Hansen T.P., and Brown M.L. Org. Lett. 5 (2003) 2865
26. Kayser M.M., Soucy C., and Favreau D. J. Org. Chem. 52 (1987) 129
27. Wako Chemicals USA, .
28. +, 343.0930. found 343.0955.
29. Palladacycle in this case refers to trans-{di(μ-acetato)-bis[ortho-(di-ortho-tolylphosphanyl)benzyl]dipalladium (II) (Below) developed by Herrmann, W. A.; Broßmer, C. B.; Öfele, K.; Reisinger, C-P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem. 1995, 107, 1989; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844{A figure is presented}.
30. Netherton M.R., and Fu G.F. Org. Lett. 3 (2001) 4295
31. Kroeger K.M., Carville K.S., and Abraham L.J. Mol. Immunol. 34 (1997) 391
32. Karimi M., Goldie L.C., Ulgiati D., and Abraham L.J. BioTechniques 42 (2007) 217
33. Miyachi H., Azuma A., Ogasawara A., Uchimura E., Watanabe N., Kobayashi Y., Kato F., Kato M., and Hashimoto Y. J. Med. Chem. 40 (1997) 2858
34. Unfortunately the Heck reaction involving 2-cyclohexen-1-one at the C2′ and C4′ positions only resulted in trace amounts of the desired olefins.