Synthetic study of VLA-4/VCAM-1 inhibitors: Synthesis and structure-activity relationship of piperazinylphenylalanine derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 3, 2008, Pages 1053-1057

  Saku, Osamu ^a   Ohta, Kiminori ^a   Arai, Eri ^a   Nomoto, Yuji ^a   Miura, Hiroko ^a   Nakamura, Hiroaki ^a   Fuse, Eiichi ^a   Nakasato, Yoshisuke ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

Piperazinylphenylalanine derivatives; VLA 4 inhibitors

Indexed keywords

PHENYLALANINE DERIVATIVE; VASCULAR CELL ADHESION MOLECULE 1; VERY LATE ACTIVATION ANTIGEN 4;

AREA UNDER THE CURVE; ARTICLE; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG EFFICACY; DRUG SYNTHESIS; IN VIVO STUDY; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; INTEGRIN ALPHA4BETA1; MICE; MOLECULAR STRUCTURE; PHENYLALANINE; PIPERAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; VASCULAR CELL ADHESION MOLECULE-1;

EID: 38749113718     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.12.014     Document Type: Article

References (21)

1. Elices M.J. In: Mousa S.A. (Ed). Cell Adhesion Molecules and Matrix Proteins: Role in Health and Diseases (1998), Springer-Verlag, Berlin 133
2. Lobb R.R., and Helmer M.E. J. Clin. Invest. 94 (1994) 1722
3. Steinman L. Nat. Rev. Drug Discov. 4 (2005) 510
4. Rice G.P.A., Hartung H.-P., and Calabresi P.A. Neurology 64 (2005) 1336
5. Miller D.H., Khan O.A., Sheremata W.A., Blumhardt L.D., Rice G.P.A., Libonati M.A., Willmer-Hulme A.J., Dalton C.M., Miszkiel K.A., and O'Connor P.W. N. Engl. J. Med 348 (2003) 15
6. Yang G.X., and Hagmann W.K. Med. Res. Rev 23 (2003) 369
7. Hagmann W.K. Curr. Top. Med. Chem. (2004) 1461
8. Sing J., Adams S., Carter M.B., Cuervo H., Lee W.-C., Lobb R.R., Pepeinsky B., Petter R., and Scott D. Curr. Top. Med. Chem. (2004) 1497
9. Holland G.W., Biediger R.J., and Vanderslice P. In: Doherty A.M. (Ed). Annual Reports in Medicinal Chemistry Vol. 37 (2002), Academic Press, New York 65-74
10. Li B., de Laszlo S.E., Kamenecka T.M., Kopka I.E., Durette P.L., Lanza Jr. T., MacCoss M., Tong S., Mumford R.A., McCauley E.D., van Riper G., Schmidt J.A., and Hagmann W.K. Bioorg. Med. Chem. Lett. 12 (2002) 2141
11. Yang G.X., Chang L.L., Truong Q., Doherty G.A., Magriotis P.A., deLaszlo S.E., Li B., MacCoss M., Kidambi U., and Egger L.A. Bioorg. Med. Chem. Lett. 12 (2002) 1497
12. Sidduri A., Tilley J.W., Lou J.P., Chen L., Kaplan G., Mennona F., Campbell R., Guthrie R., Huang T.N., Rowan K., Schwinge V., and Renzetti L.M. Bioorg. Med. Chem. Lett. 12 (2002) 2479
13. Witherington J., Bordas V., Gaiba A., Green P.M., Naylor A., Parr N., Smith D.G., Takle A.K., and Ward R.W. Bioorg. Med. Chem. Lett. 16 (2006) 2256
14. Singh J., Vlihmen H.V., Liao Y., Lee W.-C., Corbenise M., Harris M., Shu I.-H., Gill A., Cuervo J.H., Abraham W.M., and Adams S.P. J. Med. Chem. 45 (2002) 2988
15. Abraham W.M., Gill A., Ahmed A., Sielczak M.W., Lauredo I.T., Botinnikova Y., Lin K.-C., Pepinsky B., Leone D.R., Lobb R.R., and Adams S.P. Am. J. Respir. Crit. Care Med. 162 (2000) 603
16. Sircar I., Gudmundsson K.S., Martin R., Liang J., Nomura S., Jayakumar H., Teegarden B.R., Nowlin D.M., Cardarelli P.M., Mah J.R., Connell S., Griffith R.C., and Lazarides E. Bioorg. Med. Chem. 10 (2002) 2051
17. Chen L., Tilley J.W., Guthrie R.W., Mennona F., Huang T.-N., Kaplan G., Trilles R., Miklowski D., Huby N., Schwinge V., Wolitzky B., and Rowan K. Bioorg. Med. Chem. Lett. 10 (2000) 729
18. Archibald S.C., Head J.C., Gozzard N., Howat D.W., Parton T.A.H., Porter J.R., Robinson M.K., Shock A., Warrellow G.J., and Abraham W.M. Bioorg. Med. Chem. Lett. 10 (2000) 997
19. 3): 1.14-1.17 (m, 1H), 1.33-1.37 (m, 2H), 1.75-1.78 (m, 1H), 2.33 (s, 3H), 2.77-2.98 (m, 2H),3.25-3.28 (m, 10H), 4.05-4.10 (m, 1H), 4.64-4.74 (m, 1H), 6.81 (d, J = 7.6 Hz, 2H), 6.98-7.08 (m, 4H), 7.19 (d, J = 6.5 Hz, 2H), 7.49 (t, J = 8.1 Hz, 1H), 7.55 (d, J = 7.6 Hz, 2H), 7.69 (d, J = 7.3 Hz, 2H).
20. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550
21. Lombardo, L. J.; Semko, C. M.; Thorsett, E. D.; Ashwell, S.; Kreft, A.; Baudy, A. R. B.; Dressen, D. B.; Grant, F. S.; Konradi, A. W.; Pleiss M. A.; Sarantakis D. PCT Int. Appl. WO9906390, 1999.