Potent nonpeptide vasopressin receptor antagonists based on oxazino- and thiazinobenzodiazepine templates

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 11, 2004, Pages 2747-2752

  Matthews, Jay M ^a   Hoekstra, William J ^a,c   Dyatkin, Alexey B ^a   Hecker, Leonard R ^a   Hlasta, Dennis J ^a   Poulter, Brenda L ^a   Andrade Gordon, Patricia ^a   De Garavilla, Lawrence ^a   Demarest, Keith T ^b   Ericson, Eric ^b   Gunnet, Joseph W ^b   Hageman, William ^a   Look, Richard ^b   Moore, John B ^b   Reynolds, Charles H ^a   Maryanoff, Bruce E ^a  

^a Drug Discovery   (United States)

^b Drug Discovery Raritan   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE; DIURETIC AGENT; VASOPRESSIN RECEPTOR ANTAGONIST; VASOPRESSIN V2 RECEPTOR;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DIURETIC ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ADMINISTRATION, ORAL; ANIMALS; BENZODIAZEPINES; DIURETICS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MOLECULAR STRUCTURE; OXAZINES; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, VASOPRESSIN; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZINES;

EID: 2342580260     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.03.083     Document Type: Article

References (30)

1. Albright J.D., Chan P.S. Curr. Pharm. Design. 3:1997;615
2. Thibonnier M., Conarty D.M., Preston J.A., Wilkins P.L., Berti-Mattera L.N., Mattera R. Adv. Exp. Med. Biol. 449:1998;251
3. Albright J.D., Reich M.F., Santos E.G.D., Dusza J.P., Sum F.W., Venkatesan A.M., Coupet J., Chan P.S., Ru X., Mazandarani H., Bailey T. J. Med. Chem. 41:1998;2442
4. Aranapakam V., Albright J.D., Grosu G.T., Chan P.S., Coupet J., Saunders T., Ru X., Mazandarani H. Bioorg. Med. Chem. Lett. 9:1999;1733
5. Martinez-Castelao A. Curr. Opin. Invest. Drugs. 2:2001;525
6. Albright J.D., Santos E.G.D., Dusza J.P., Chan P.S., Coupet J., Ru X., Mazandarani H. Bioorg. Med. Chem. Lett. 10:2000;695
7. Ashwell M.A., Bagli J.F., Caggiano T.J., Chan P.S., Molinari A.J., Palka C., Park C.H., Rogers J.F., Sherman M., Trybulski E.J., Williams D.K. Bioorg. Med. Chem. Lett. 10:2000;783
8. Ogawa H., Yamashita H., Kondo K., Yamamura Y., Miyamoto H., Kan K., Kitano K., Tanaka M., Nakaya K., Nakamura S., Mori T., Tominaga M., Yabuuchi Y. J. Med. Chem. 39:1996;3547
9. Matsuhisa A., Taniguchi N., Koshio H., Yatsu T., Tanaka A. Chem. Pharm. Bull. 48:2000;21
10. Trybulski E.J. Annu. Rep. Med. Chem. 36:2001;159
11. Oprea T.I. J. Comput.-Aided Mol. Design. 14:2000;251
12. Walters W., Patrick A., Murcko M.A. Curr. Opin. Chem. Biol. 3:1999;384
13. Matthews, J. M.; Dyatkin, A. B.; Evangelisto, M.; Gauthier, D. A.; Hecker, L. R.; Hoekstra, W. J.; Poulter, B. L.; Maryanoff, B. E. Tetrahedron: Asymmetry 2004, 15, in press
14. 6
15. 6
16. Kogami Y., Okawa K. Bull. Chem. Soc. Jpn. 60:1987;2963
17. 11
18. Dyatkin A.B., Freedman T.B., Cao X., Dukor R.K., Maryanoff B.E., Maryanoff C.A., Matthews J.M., Shah R.D., Nafie L.A. Chirality. 14:2002;215
19. 3H]-AVP
20. 2d
21. 2) concentrations were measured
22. 2a
23. 2, respectively. The isotropic thermal parameters of the remaining hydrogens were fixed at values 1.2 (nonmethyl) or 1.5 (methyl) times the equivalent isotropic thermal parameter of the attached carbon atom. Atomic coordinates for this structure are available from the authors on request
24. Hassner A., Amit B., Marks V., Gottlieb H.E. J. Org. Chem. 68:2003;6853
25. Maestro, 5.1 ed., Schrodinger Inc. (Portland, OR), 2003
26. Jorgensen W.L., Tirado-Rives J. J. Am. Chem. Soc. 110:1988;1657
27. Qui D., Shenkin P.S., Hollinger F.P., Still W.C. J. Phys. Chem. A. 101:1997;3005
28. Chang G., Guida W.C., Still W.C. J. Am. Chem. Soc. 111:1989;4379
29. For some molecular modeling studies, see: Gieldon A., Kazmierkiewicz R., Slusarz R., Ciarkowski J. J. Comput.-Aided Mol. Design. 15:2001;1085
30. 1/2 of 3.7 h