A quick diversity-oriented amide-forming reaction to optimize p-subsite residues of HIV protease inhibitors

Chemistry and Biology

Volumn 9, Issue 8, 2002, Pages 891-896

  Brik, Ashraf ^a   Lin, Ying Chuan ^a   Elder, John ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PROTEINASE INHIBITOR;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG RESISTANCE; DRUG SCREENING; GENETICS; HUMAN; IC 50; METHODOLOGY; MUTATION; STRUCTURE ACTIVITY RELATION;

AMIDES; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG EVALUATION, PRECLINICAL; DRUG RESISTANCE; HIV PROTEASE INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MUTATION; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0036669203     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(02)00184-9     Document Type: Article

References (16)

1. Huff J.R., Kahn J. Discovery and clinical development of HIV-1 protease inhibitors. Adv. Protein Chem. 56:2001;213-251.
2. Babine R.E., Bender S.L. Molecular recognition of protein-ligand complexes. Applications to drug design Chem. Rev. 97:1997;1359-1472.
3. Wlodawer A., Erickson J.W. Structure-based inhibitors of HIV-1 protease. Annu. Rev. Biochem. 62:1993;543-585.
4. Erickson J.W., Burt S.K. Structural mechanisms of HIV drug resistance. Annu. Rev. Pharmacol. Toxicol. 36:1996;545-571.
5. Schinazi R.F., Larder B.A., Mellors J.W. Mutations in retroviral genes associated with drug resistance. Int. Antiviral News. 5:1997;129-142.
6. Field G.B. Coupling reagents and activation. Albericio F., Carpino L.A. Methods in Enzymology. 1997;Acadmic Press, New York. 104-126.pp.
7. Yoshimura K., Kato R., Kavlick M.F., Nguyen A., Maroun V., Maeda K., Hussain K.A., Ghosh A.K., Gulnik S.V., Erickson J.W.et al. A potent human immunodeficiency virus type 1 protease inhibitor, UIC-94003 (TMC-126), and selection of a novel (A28S) mutation in the protease active site. J. Virol. 76:2002;1349-1358.
8. Rano T.A., Cheng Y., Huening T.T., Zhang F., Schleif W.A., Gabryelski L., Olsen D.B., Kuo L.C., Lin J.H., Xu X.et al. Combinatorial diversification of Indinavir. In vivo mixture dosing of an HIV protease inhibitor library Bioorg. Med. Chem. Lett. 10:2000;1527-1530.
9. Kick E.K., Ellman J.A. Expedient method for the solid-phase synthesis of aspartic acid protease inhibitors directed toward the generation of libraries. J. Med. Chem. 38:1995;1427-1430.
10. Wang G.T., Sam L., Wideburg N., Krafft G.A., Kempf D.J. Synthetic chemical diversity. solid phase synthesis of libraries of C2 symmetric inhibitors of HIV-1 PRotease containing diamino diol and diamino alcohol cores J. Med. Chem. 38:1995;2995-3002.
11. Le V.-D., Mak C.C., Lin Y.-C., Elder J.H., Wong C.-H. Structure-activity studies of FIV and HIV-1 PRotease inhibitors containing allophenylnorstatine. Bioorg. Med. Chem. 9:2001;1185-1195.
12. Mak C.C., Le V.-D., Lin Y.-C., Elder J.H., Wong C.-H. Design, synthesis, and biological evaluation of HIV/FIV protease inhibitors incorporating a conformationally constrained macrocycle with a small P3′ residue. Bioorg. Med. Chem. Lett. 11:2001;219-222.
13. Lee T., Le V.-D., Lim D., Lin Y.-C., Morris G.M., Wong A.L., Olson A.J., Elder J.H., Wong C.-H. Development of a new type of protease inhibitors, efficacious against FIV and HIV variants. J. Am. Chem. Soc. 121:1999;1145-1155.
14. Lee T., Laco G.S., Torbett B.E., Fox H.S., Lerner D.L., Elder J.H., Wong C.-H. Analysis of the S3 and S3′ subsite specificities of feline immunodeficiency virus (FIV) protease. development of a broad-based protease inhibitor efficacious against FIV, SIV, and HIV in vitro and ex vivo Proc. Natl. Acad. Sci. USA. 95:1998;939-944.
15. Hosur M.V., Bhat T.N., Kempf D.J., Baldwin E.T., Liu B., Gilnik S., Wideburg N.E., Norbeck D.W., Appelt K., Erickson J.W. Influence of stereochemistry on activity and binding modes for C2 symmetry-based diol inhibitors of HIV-1 protease. J. Am. Chem. Soc. 116:1994;847-855.
16. Ghosh A.K., Bilcer G., Schiltz G. Syntheses of FDA approved HIV protease inhibitors. Synthesis. 15:2001;2203-2229.