Solid phase synthesis of phosphinic acid endothelin converting enzyme inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 12, 1996, Pages 1323-1326

  Lloyd, John ^a   Schmidt, Joan B ^a   Hunt, John T ^a   Barrish, Joel C ^a   Little, Deborah K ^a   Tymiak, Adrienne A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENDOTHELIN CONVERTING ENZYME; ENDOTHELIN RECEPTOR; MEMBRANE METALLOENDOPEPTIDASE; METALLOPROTEINASE INHIBITOR; PHOSPHINIC ACID DERIVATIVE; PHOSPHORAMIDON;

ARTICLE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENDOTHELIUM CELL; ENZYME INHIBITION; HUMAN; HUMAN CELL; PEPTIDE SYNTHESIS; SOLID PHASE EXTRACTION; UMBILICAL VEIN;

EID: 0030005512     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00227-2     Document Type: Article

References (16)

1. Yanagisawa, M.; Kurihara, H.; Kimura, S.; Tomobe, Y.; Kobayashi, M.; Mitsui, y.; Yazaki, Y.; Katsutoshi, G.; Masaki, T. Nature. 1988, 332, 411.
2. (a) Doherty, A. M. J. Med. Chem. 1992, 35, 1493.
3. (b) Remuzzi, G.; Benigni, A. Lancet. 1993, 342, 589.
4. (a) Sokolovsky, M.; Ambar, I.; Galron, R. J. Biol. Chem. 1992. 267, 20551.
5. (b) Moreland, S.; McMullen, D. M.; Delaney, C. L.; Lee, V. G.; Hunt, J. T. Biochem. Biophys. Res. Commun. 1992, 184, 100.
6. (c) Sakurai, T.; Yanagisawa, M.; Masaki, T. Trends Pharm. Sci. 1992, 13, 103.
7. Opgenorth, T. J.; Wu-Wong, J. R.; Shiosaki, K. FASEB J. 1992, 6, 2653.
8. Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. J. Chem. Soc. Perkin Trans 1. 1984, 2845
9. Thottathil, J. K.; Ryono, D. E.; Przybyla, C. A.; Moniot, J. L.; Neubeck, R. Tetrahedron Lett. 1984, 24, 4741.
10. Campagne, J-M.; Coste, J.; Guilliou, L.; Heitz, A.; Jouin, P. Tetrahedron Lett. 1993, 34, 4181.
11. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205. Coupling conditions typically were 1.5 equiv. 5, 1.5 equiv. PyBOP, 3 equiv diisopropylethylamine in DMF, 25°.
12. Clavage conditions were 50% reagent K (82.5% TFA, 5% water, 5% thiophenol, 5% phenol, 2.5% ethanedithiol), 50% dichloromethane.
13. Cleavage conditions were 5 equiv. tryptamine in 2.5% water, 47.5% TFA, and 50% dichloromethane.
14. Little, D. K.; Floyd, D. M.; Tymiak, A. A. J. Pharm. Tox. Meth. 1994, 31, 199. Subsequent to our studies, a phophorimidon sensitive ECE was cloned. Dong, X.; Emoto, N.; Giaid, A.; Slaughter, C.; Kaw, S.; deWit, D.; Yanagisawa, M. Cell, 1994, 78, 473.
15. Little, D. K.; Floyd, D. M.; Tymiak, A. A. J. Pharm. Tox. Meth. 1994, 31, 199. Subsequent to our studies, a phophorimidon sensitive ECE was cloned. Dong, X.; Emoto, N.; Giaid, A.; Slaughter, C.; Kaw, S.; deWit, D.; Yanagisawa, M. Cell, 1994, 78, 473.
16. Dickinson, K. E. J.; Tymiak, A. A.; Cohen, R. B.; Liu, E. C-K.; Webb, M.; Hedberg, A. Biochem. Biophys. Res. Commun. 1991, 176, 423.