Synthesis of 3H-labeled 2-hydroxy-N-[(1,3,3-trimethyl-[4,5,6-3H]cyclohexyl)methyl]-5-azidobenzamide, a photoaffinity analog of an influenza fusion inhibitor

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 42, Issue 10, 1999, Pages 965-974

  Dischino, Douglas D ^a   Cianci, Christopher ^a   Krystal, Mark ^a   Meanwell, Nicholas A ^a   Morimoto, Hiromi ^b   Pearce, Bradley C ^a   Williams, Philip ^b   Yu, Kuo Long ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

Hemagglutinin protein; Influenza; Photoaffinity label; Tritium

Indexed keywords

CHLORINE COMPOUNDS;

ACID CHLORIDES; CYCLOHEXYL; FUSION INHIBITORS; HEMAGGLUTININ PROTEIN; INFLUENZA; PHOTOAFFINITY; PHOTOAFFINITY ANALOGUES; PHOTOAFFINITY LABEL; TRIMETHYL; TRITIATION;

BIOSYNTHESIS;

BENZAMIDE DERIVATIVE; SALICYLIC ACID DERIVATIVE; TRITIUM;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFLUENZA VIRUS; RADIOCHEMISTRY; VIRUS INHIBITION;

INFLUENZA VIRUS; TRITIUM;

EID: 0032870105     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1344(199910)42:10<965::AID-JLCR255>3.0.CO;2-K     Document Type: Article

References (15)

1. Murphy, B.R. and Webster, R.G. - in Virology, 2nd ed., Ed. Fields, B.N., and Knipe, D.M., Raven Press, 1091(1990).
2. Palese, P. - Cell 10: 1 (1977).
3. Wiley, D.C. and Skehel, J.J. - Ann. Rev. Biochem. 56: 365 (1987).
4. White, J.M. - Ann. Rev. Physiol. 52: 675 (1990).
5. White, J.M. - Science 258: 917 (1992).
6. Helenius, A. - Cell 69: 577 (1992).
7. Stegmann, T. and Helenius, A. - in Viral Fusion Mechanisms, Ed. Bentz, J., CRC Press, 89 (1993).
8. Luo, G., Colonno, R. and Krystal, M. - Virology 226: 66, (1996).
9. Luo, G., Torri, A., Harte, W.E., Danetz, S., Cianci, C., Tiley, L., Day, S., Mullaney, D., Yu, K.-L., Ouellet, C., Dextraze, P., Meanwell, N., Colonno, R. and Krystal, M. - J. Virol. 71: 4062 (1997).
10. Yu, K.-L., Cianci, C., Combrink, K., Deshpande, M., Grant-Young, K., Gulgeze, B., Krystal, M., Meanwell, N., Pearce, B.C., Trehan, A., and Wei, J. -Manuscripts in preparation.
11. Schwartz, M.A. - Anal. Biochem. 149: 142 (1985).
12. Williams, P.G., Than, C., Rabbani, S., Long, M.A. and Garnett, J.L. - J. Labelled Compd. Radiopharm. 36: 1 (1995).
13. Williams, P.G., Morimoto, H. and Wemmer, D.E. - J. Am. Chem. Soc. 110: 8038 (1988).
14. Cianci, C., Yu, K.-L., Dischino, D., Harte, W., Luo, G., Deshpande, M., Colonno, R.J., Meanwell, N.A. and Krystal, M. - J. Virol. 73: 1785 (1999).
15. The preparation of this acid chloride was conducted in an amber flask under reduced lighting. In a typical preparation of the acid chloride, the corresponding azido acid (17.1 mg, 0.080 mmol) was dissolved methylene chloride (0.4 mL) and to this solution was added DMF (4 μl) and oxalyl chloride (18 μl) and the reaction allowed to stir in a sealed flask for 2h at 0°C. After 2h, the solution was evaporated to dryness under a nitrogen stream and the residue resuspended in methylene chloride (0.5 mL) and used immediately.