Non-peptide αvβ3 antagonists. Part 5: Identification of potent RGD mimetics incorporating 2-aryl β-amino acids as aspartic acid replacements

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 23, 2002, Pages 3483-3486

  Brashear, Karen M ^a   Hunt, Cecilia A ^a   Kucer, Brian T ^a   Duggan, Mark E ^a   Hartman, George D ^a   Rodan, Gideon A ^a   Rodan, Sevgi B ^a   Leu, Chi Tai ^a   Prueksaritanont, Thomayant ^a   Fernandez Metzler, Carmen ^a   Barrish, Andrea ^a   Homnick, Carl F ^a   Hutchinson, John H ^a   Coleman, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; BETA AMINO ACID; AMINO ACID; ARGINYL-GLYCYL-ASPARTIC ACID; ARGINYLGLYCYLASPARTIC ACID; BIOMIMETIC MATERIAL; ESTER; OLIGOPEPTIDE; VITRONECTIN RECEPTOR;

ARTICLE; DRUG IDENTIFICATION; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; DOG; DRUG ANTAGONISM; DRUG SCREENING; HUMAN; IC 50; METABOLISM; PROTEIN BINDING; SYNTHESIS;

AMINO ACIDS; ANIMALS; ASPARTIC ACID; BIOMIMETIC MATERIALS; DOGS; DRUG EVALUATION, PRECLINICAL; ESTERS; HUMANS; INHIBITORY CONCENTRATION 50; OLIGOPEPTIDES; PROTEIN BINDING; RECEPTORS, VITRONECTIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 18644384406     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00743-6     Document Type: Article

References (25)

1. (a) Compston J.E. Drugs. 53:1997;727
2. (a) Compston J.E. Drugs. 53:1997;727 (b) Kanis J.A., Delmas P., Burckhardt P., Cooper C., Torgerson D. Osteoporosis Int. 7:1997;390.
3. Duong L.T., Rodan G.A. Front. Biosci. 3:1998;757.
4. (a) Crippes B.A., Engleman V.W., Settle S.L., Delarco J., Ornberg R.L., Helfrich M.H., Horton M.A., Nikols G.A. Endocrinology. 137:1996;918
5. (b) Yamamoto M., Fisher J.E., Gentile M., Seedor J.G., Leu C.T., Rodan S.B., Rodan G.A. Endocrinology. 139:1998;1411
6. (c) Lark M.W., Stroup G.B., Hwang S.M., James I.E., Rieman D.J., Drake F.H., Bradbeer J.N., Mathur A., Erhard K.F., Newlander K.A., Ross S.T., Salyers K.L., Smith B.R., Miller W.H., Huffman W.F., Gowen M. J. Pharm. Exp. Therap. 291:1999;612.
7. Coleman, P. J.; Askew, B. C.; Hutchinson, J. H.; Whitman, D. B.; Perkins, J. J.; Hartman, G. D.; Rodan, G. A.; Leu, C. T.; Prueksaritanont, T.; Fernandez-Metzler, C.; Merkle, K. M.; Lynch, R.; Lynch, J. J.; Rodan, S. B.; Duggan, M. E. Bioorg. Med. Chem. Lett. 2002, 12, 2463.
8. (a) Duggan M.E., Naylor-Olsen A.M., Perkins J.J., Anderson P.S., Chang C.T.-C., Cook J.J., Gould R.J., Ihle N.C., Hartman G.D., Lynch J.J., Lynch R.J., Manno P.D., Schaffer L.W., Smith R.L. J. Med. Chem. 38:1995;3332
9. (b) Askew B.C., McIntyre C.A., Hunt C.A., Claremon D.A., Gould R.J., Lynch R.J., Armstrong D.J. Bioorg. Med. Chem. Lett. 6:1996;339.
10. (a) Hartman G.D., Egbertson M.S., Halczenko W., Laswell W.L., Duggan M.E., Smith R.L., Naylor A.M., Manno P.D., Lynch R.J., Zhang G., Chang C.T.-C., Gould R.J. J. Med. Chem. 35:1992;4640
11. (b) Egbertson M.S., Chang C.T.-C., Duggan M.E., Gould R.J., Halczenko W., Hartman G.D., Laswell W.L., Lynch J.J., Lynch R.J., Manno P.D., Naylor A.M., Prugh J.D., Ramjit D.R., Sitko G.R., Smith R.S., Turchi L.M., Zhang G. J. Med. Chem. 37:1994;2537
12. (c) Egbertson M.S., Hartman G.D., Gould R.J., Bednar B., Bednar R.A., Cook J.J., Gaul S.L., Holahan M.A., Libby L.A., Lynch J.J. Jr., Sitko G.R., Stranieri M.T., Vassallo L.M. Bioorg. Med. Chem. Lett. 6:1996;2519
13. (d) Askew B.C., Bednar R.A., Bednar B., Claremon D.A., Cook J.J., McIntyre C.J., Hunt C.A., Gould R.J., Lynch R.J., Lynch J.J., Gaul S.L., Stranieri M.T., Sitko G.R., Holahan M.A., Glass J.D., Hamill T., Gorham L.M., Prueksaritanont T., Baldwin J.J., Hartman G.D. J. Med. Chem. 40:1997;1779.
14. Duggan M.E., Duong L.T., Fisher J.E., Hamill T.G., Hoffman W.F., Huff J.R., Ihle N.C., Leu C.-T., Nagy R.M., Perkins J.J., Rodan S.B., Wesolowski G., Whitman D.B., Zartman A.E., Rodan G.A., Hartman G.D. J. Med. Chem. 43:2000;3736.
15. Coleman P.J., Hutchinson J.H., Hunt C.A., Lu P., Delaporte E., Rushmore T. Tetrahedron Lett. 41:2000;5803.
16. Ikeda K., Achiwa K., Sekiya M. Tetrahedron Lett. 24:1983;4707.
17. Wiseman J.R., Pletcher W.A. J. Am. Chem. Soc. 92:1970;956.
18. Turner J.A. J. Org. Chem. 48:1983;3401.
19. (a) 3-Substituted β-alanines: Quinoline: Cole, D. C. Tetrahedron 1994, 50, 9517.
20. (b) Dihydrobenzofuranyl: See ref 8.
21. (c) Fluorophenyl: Adapted from chemistry as described in Rico, J. G.; Lindmark, R. J.; Rogers, T. E.; Bovy, P. R. J. Org. Chem. 1993, 58, 7948.
22. (d) Phenyl: Johnson, T. B.; Livac, J. E. J. Am. Chem. Soc. 1936, 58, 299.
23. (e) Tetrahydronaphthyridinyl side chains: Tetrahydronaphthyridinyl pentanoic acid: See ref 4.
24. (f) 3-Cyclopropyl: Wang, J.; Whitman, D. B.; Hutchinson, J. H.; Halczenko, W.; Duggan, M. E.; Hartman, G. D.; Leu, C. T.; Rodan, S. B.; Rodan, G. A.; Kimmel, D. B.; Prueksaritanont, T. Personal communication.
25. 125 Iodophenylsulfonylamino-β-alanine. For protocol, see: Duggan, M. E.; Hartman, G. D.; Hoffman, W. F.; Meissner, R. S.; Perkins, J. J.; Askew, B. C.; Coleman, P. J.; Hutchinson, J. H.; Naylor-Olsen, A. M. US Patent 5,981,546, 1999.