Design and synthesis of a vialinin A analog with a potent inhibitory activity of TNF-α production and its transformation into a couple of bioprobes

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 7, 2012, Pages 2385-2387

  Ye, Yue Qi ^a,b   Onose, Jun Ichi ^b   Abe, Naoki ^b   Koshino, Hiroyuki ^a   Takahashi, Shunya ^a  

^a RIKEN   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

Author keywords

Biotinylated bioprobe; Dimethyl analog of vialinin A; Fluorescent bioprobe; Inhibitor of TNF production; Vialinin A

Indexed keywords

5',6' DIMETHYL 1,1':4'1'' TERPHENYL 2',3',4,4'' TETRAOL; ANTINEOPLASTIC AGENT; PHENOL DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOTINYLATION; CLICK CHEMISTRY; CYTOKINE PRODUCTION; DRUG DESIGN; DRUG IDENTIFICATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; FLUOROSCOPY; MOLECULAR PROBE; NONHUMAN; RAT; SUZUKI REACTION;

ANIMALS; BIOTINYLATION; CELL LINE, TUMOR; DRUG DESIGN; FLUORESCENCE; LEUKEMIA; MOLECULAR PROBES; MOLECULAR STRUCTURE; RATS; TERPHENYL COMPOUNDS; TUMOR NECROSIS FACTOR-ALPHA; XYLENES;

RATTUS;

EID: 84858700020     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.02.034     Document Type: Article

References (21)

1. C. Xie, H. Koshino, Y. Esumi, S. Takahashi, K. Yoshikawa, and N. Abe Biosci. Biotechnol. Biochem. 69 2005 2326
2. N. Radulovic, D.N. Quang, T. Hashimoto, M. Nukada, and Y. Asakawa Phytochemistry 66 2005 1052
3. T. Norikura, K. Fujiwara, T. Narita, S. Yamaguchi, Y. Morinaga, K. Iwai, and H. Matsue J. Agric. Food Chem. 59 2011 6974
4. J. Onose, C. Xie, Y.-Q. Ye, S. Takahashi, H. Koshino, K. Yasunaga, N. Abe, and K. Yoshikawa Biol. Pharm. Bull. 31 2008 831
5. J.R. Gordon, P.R. Burd, and S.J. Galli Immunol. Today 11 1990 458
6. P. Vassalli Annu. Rev. Immunol. 10 1992 411
7. J. Sieper, and J. Braun Exper. Opin. Emerg. Drugs 2 2002 235
8. S.T. Holgate Cytokine 28 2004 152
9. F.M. Brennan, D. Chantry, A. Jackson, R. Maini, and M. Feldmann Lancet 2 8657 1989 244
10. R. Maini, E.W. St Clair, F. Breedveld, D. Furst, J. Kalden, M. Weisman, J. Smolen, P. Emery, G. Harriman, M. Feldmann, and P. Lipsky Lancet 354 9194 1999 1932
11. C. Xie, H. Koshino, Y. Esumi, J. Onose, K. Yoshikawa, and N. Abe Bioorg. Med. Chem. Lett. 16 2006 5424
12. Y.-Q. Ye, H. Koshino, J. Onose, C. Negishi, K. Yoshikawa, N. Abe, and S. Takahashi J. Org. Chem 74 2009 4642
13. Y.-Q. Ye, H. Koshino, J. Onose, K. Yoshikawa, N. Abe, and S. Takahashi Org. Lett 9 2007 4131
14. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
15. L. Horner, and K. Sturm Liebigs Ann. Chem. 597 1955 1
16. B.E. Huff, T.M. Koenig, D. Mitchell, and M.A. Staszak Organic Syntheses 2004 Wiley&Sons NewYork pp.102
17. Kawada, K.; Ohtani, M.; Suzuki, R.; Arimura, A. US-Patent, 7,101,915, 2006.
18. Y.-Q. Ye, H. Koshino, J. Onose, K. Yoshikawa, N. Abe, and S. Takahashi Org. Lett. 11 2009 5074
19. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
20. I.A. Inverarity, R.F.H. Viguier, P. Cohen, and A.N. Hulme Bioconjugate Chem. 18 2007 1593
21. D. Charon, M. Mondange, J.-F. Pons, K. Le Blay, and R. Chaby Bioorg. Med. Chem. 6 1998 755