Structure-activity relationships for a series of thiobenzamide influenza fusion inhibitors derived from 1,3,3-trimethyl-5-hydroxy-cyclohexylmethylamine

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 23, 2002, Pages 3379-3382

  Yu, Kuo Long ^a   Torri, Albert F ^a   Luo, Guangxiang ^a   Cianci, Christopher ^a   Grant Young, Katharine ^a   Danetz, Stephanie ^a   Tiley, Lawrence ^a   Krystal, Mark ^a   Meanwell, Nicholas A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,3 TRIMETHYL 5 HYDROXYCYCLOHEXYLMETHYLAMINE; ANTIVIRUS AGENT; THIOBENZAMIDE DERIVATIVE; UNCLASSIFIED DRUG; BMY 27709; METHYLAMINE; QUINOLIZINE DERIVATIVE; THIOAMIDE; THIOBENZAMIDE;

ANTIVIRAL ACTIVITY; ARTICLE; CELL VIABILITY; DRUG POTENCY; IC 50; INFLUENZA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; VIRUS INHIBITION; ANIMAL; CELL CULTURE; CHEMISTRY; DOG; DRUG EFFECT; DRUG SCREENING; HEMOLYSIS; MEMBRANE FUSION; ORTHOMYXOVIRUS; STEREOISOMERISM;

ANIMALS; ANTIVIRAL AGENTS; CELLS, CULTURED; DOGS; DRUG EVALUATION, PRECLINICAL; HEMOLYSIS; INHIBITORY CONCENTRATION 50; MEMBRANE FUSION; METHYLAMINES; ORTHOMYXOVIRIDAE; QUINOLIZINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIOAMIDES;

EID: 0036888518     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00761-8     Document Type: Article

References (20)

1. Reid A.H., Fanning T.G., Hultin J.V., Taubenberger J.K. Proc. Natl. Acad. Sci. 96:1999;1651.
2. Treanor, J. J. in Principles and Practice of Infectious Diseases; Mandell, G. L; Bennett, J. E.; Dolin, R., Eds.; Churchill Livingstone: Philadelphia, 2000; 5th Ed., Vol. 2, pp 1823-1848.
3. Meanwell, N. A.; Krystal, M. Drug Disc. Today 1996, 1, 316; 1996, 1, 388.
4. Meanwell, N. A.; Krystal, M. Drug Disc. Today 1996, 1, 316; 1996, 1, 388.
5. Carr C.M., Kim P.S. Science. 266:1994;234.
6. Luo G.-X., Colonno R., Krystal M. Virology. 226:1996;66.
7. Luo G.-X., Torri A., Harte W.E., Danetz S., Cianci C., Tiley L., Day S., Mullaney D., Yu K.-L., Quellet C., Dextraze P., Meanwell N.A., Colonno R., Krystal M. J. Virol. 71:1997;4062.
8. Cianci C., Yu K.-L., Dischino D.D., Harte W., Deshpande M., Luo G.-X., Colonno R.J., Meanwell N.A., Krystal M. J. Virol. 73:1999;1785.
9. Yu K.-L., Ruediger E., Luo G., Cianci C., Danetz S., Tiley L., Trehan A.K., Monkovic I., Pearce B., Martel A., Krystal M., Meanwell N.A. Bioorg. Med. Chem. Lett. 9:1999;2177.
10. Combrink K.D., Gulgeze H.B., Yu K.-L., Pearce B.C., Trehan A.K., Wei J., Deshpande M., Krystal M., Torri A., Luo G., Cianci C., Danetz S., Tiley L., Meanwell N.A. Bioorg. Med. Chem. Lett. 10:2000;1649.
11. Deshpande M., Wei J., Luo G.-X., Cianci C., Danetz S., Tiley L., Pearce B.C., Krystal M., Yu K.-L., Meanwell N.A. Bioorg. Med. Chem. Lett. 11:2001;2393.
12. (a) Scheibye S., Pedersen B.S., Lawesson S.-O. Bull. Soc. Chim. Belg. 87:1978;229
13. (b) Thomsen I., Clausen K., Scheibye S., Lawesson S.-O. Org. Synth. 62:1984;158.
14. (a) Laurence C., Berthelot M., Le Questel J.-Y., El Ghomari M.J. J. Chem. Soc. Perkin Trans. 2. 1995;2075
15. (b) Min B.K., Lee H.-J., Choi Y.S., Park J., Yoon C.-J., Yu J.-A. J. Mol. Struct. 471:1998;283
16. (c) Steiner T. Angew. Chem. Int. Ed. 41:2002;48.
17. (a) Fritz, J. E. Kaldor, S. W.; Kyle, J. A.; Munroe, J. E. WO 9741846 to Eli Lilly and Company.
18. (b) Munroe, J. E.; Kyle, J. A.; Tang, J.; Sachs, R. S.; Kaldor, S. W.; Fritz, J. E. 218th ACS National Meeting, New Orleans, LA, Aug. 22-26, 1999; MEDI-278.
19. Plotch S.J., O'Hara B., Morin J., Palant O., LaRocque J., Bloom J.D., Lang S.A., Digrandi M.J., Bradley M., Nilakantan R., Gluzman Y. J. Virol. 73:1999;140.
20. Yoshimoto J., Kakui M., Iwasaki H., Fujiwara T., Sugimoto H., Hattori N. Arch. Virol. 144:1999;865.