Novel spirocyclic pyrrolidones as P2/P1 mimetics in potent inhibitors of HIV-1 protease

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 23, 2002, Pages 3431-3433

  Kazmierski, Wieslaw M ^a   Furfine, Eric ^a   Spaltenstein, Andrew ^a   Wright, Lois L ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIBROMOPENTANE; 2 PYRROLIDONE DERIVATIVE; PENTANE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BIOMIMETIC MATERIAL; LACTAM; SPIRO COMPOUND;

ALKYLATION; ARTICLE; CONJUGATE; DRUG SYNTHESIS; CHEMISTRY;

HUMAN IMMUNODEFICIENCY VIRUS 1;

ALKYLATION; ANTI-HIV AGENTS; BIOMIMETIC MATERIALS; HIV PROTEASE INHIBITORS; LACTAMS; PYRROLIDINONES; SPIRO COMPOUNDS;

EID: 0036888380     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00733-3     Document Type: Article

References (14)

1. Kim E.E., Baker C.T., Dwyer M.D., Murcko M.A., Rao B.G., Tung R.D., Navia M.A. J. Am. Chem. Soc. 117:1995;1181.
2. Askin D., Eng K.K., Rossen K., Purick R.M., Wells K.M., Volante R.P., Reider P.J. Tetrahedron Lett. 35:1994;673.
3. Tung, R. D.; Salituro, F. G.; Deininger, D. D.; Bhisetti, G. R.; Baker, C. T.; Spaltenstein, A.; Kazmierski, W. M. WO 9727180. CAN 132:322087.
4. Salituro F.G., Baker C.T., Court J.J., Deininger D.D., Kim E.E., Li B., Novak P.M., Rao B.G., Pazhanisamy S., Porter M.D., Schairer W.C., Tung R.D. Bioorg. Med. Chem. Lett. 8:1998;3637.
5. Spaltenstein A., Cleary D., Bock B., Kazmierski W., Furfine E., Wright L., Hazen R., Andrews W., Almond M., Tung R., Salituro F. Bioorg. Med. Chem. Lett. 10:2000;1159.
6. Fritch P.C., Kazmierski W.M. Synthesis. 1:1999;112.
7. Fritch, P. C.; Kazmierski, W. M. Peptidomimetics Protocols Humana: Totowa, 1999; p 281.
8. Padwa A., Hertzog D.L., Nadler W.R., Osterhout M.H., Price A.T. J. Org. Chem. 59:1994;1418.
9. Nakagawa Y., Kanai M., Nagaoka Y., Tomioka K. Tetrahedron. 54:1998;10295.
10. Charrier J.-D., Duffy J.E.S., Hitchcock P.B., Young D.W. Tetrahedron Lett. 39:1998;2199.
11. Related transformations of cyclic carbamates from β-hydroxy-N-Boc amines have been described, e.g. Pihko A.J., Nicolaou K.C., Koskinen A.M.P. Tetrahedron: Asymmetry. 12:2001;937.
12. 3) δ 169.8, 152.3, 134.8, 126.4, 125.2, 123.2, 77.3, 76.0, 48.6, 38.8, 29.3, 25.9, 25.3, 25.0. MS: m/z 372.2 (M+Na).
13. +).
14. Maschera B., Darby G., Palu G., Wright L.L., Tisdale M., Myers R., Blair E.D., Furfine E.S. J. Biol. Chem. 271:1996;33231.