Classical bioisosteres

Bioisosteres in Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 15-29

  Barillari, Caterina ^a   Brown, Nathan ^a  

^a IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

Author keywords

Bioisosteres; Bioisosterism; Functional groups; Isosterism; Pharmacokinetics; Ring equivalents

Indexed keywords

PHARMACOKINETICS;

BIOISOSTERES; BIOISOSTERISM; ISOSTERISM;

FUNCTIONAL GROUPS;

EID: 84900300151     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527654307.ch2     Document Type: Chapter

References (26)

1. Langmuir, I. (1919) Isomorphism, isosterism and covalence. Journal of the American Chemical Society, 41, 1543-1559.
2. Grimm, H.G. (1925) On construction and sizes of non-metallic hydrides. Zeitschrift für Elektrochemie und Angewandte Physikalische Chemie, 31, 474;
3. 1928, 34, 430;
4. 1934, 47, 53,-594.
5. Erlenmeyer, H. and Leo, M. (1932) On pseudoatoms. Helvetica Chimica Acta, 15, 1171.
6. Friedman, H.L. (1951) Influence of isosteric replacements upon biological activity. NAS-NRS Publication No. 206, NAS-NRS, Washington, DC, p. 295.
7. Thornber, C.W. (1979) Isosterism and molecular modification in drug design. Chemical Society Reviews, 8, 563-580.
8. Burger, A. (1970) Medicinal Chemistry, 2nd edn (ed. A. Burger), Wiley-Interscience, New York.
9. Patani, G.A. and LaVoie, E.J. (1996) Bioisosterism: a rational approach in drug design. Chemical Reviews, 96, 3147-3176.
10. Moreira, L. and Barreiro, E.J. (2005) Bioisosterism: a useful strategy for molecular modification and drug design. Current Medicinal Chemistry, 12, 23-49.
11. Xiaoqi, C. and Weibo,W. (2003) The use of bioisosteric groups in lead optimization. Annual Reports in Medicinal Chemistry, 38, 333-346.
12. Olesen, P.H. (2001) The use of bioisosteric groups in lead optimization. Current Opinion in Drug Discovery & Development, 4 (4), 471-478.
13. Meanwell, N.A. (2011) Synopsis of some recent tactical application of bioisosteres in drug design. Journal of Medicinal Chemistry, 54, 2529-2591.
14. 1 imidazoline receptor selective ligand with hypotensive activity. Journal of Medicinal Chemistry, 44, 1588-1593.
15. Counsell, R.E., Klimstra, P.D., Nysted, L.N., and Ranney, R.E. (1965) Hypocholesterolemic agents. V. Isomeric azacholesterols. Journal of Medicinal Chemistry, 8, 45-48.
16. Barnes, M.J., Conroy, R., Miller., D.J., Mills, J.S., Montana, J.G., Pooni, P.K., Showell, G.A., Walsh, L.M., and Warneck, J.B.H. (2007) rimethylsilylpyrazoles as novel inhibitors of p38 MAP kinase: a new use of silicon bioisosteres in medicinal chemistry. Bioorganic & Medicinal Chemistry Letters, 17, 354-357.
17. Wang, T., Yin, Z., Zhang, Z., Bender, J.A., Yang, Z., Johnson, G., Yang, Z., Zadjura, L.M., D'Arienzo, C.J., Parker DiGiugno, D., Gesenberg, C., Yamanaka, G.A., Gong, Y.-F., Ho, H.-T., Fang, H., Zhou, N., McAuliffe, B.V., Eggers, B.J., Fan, L., Nowicka-Sans, B., Dicker, I.B., Gao, Q., Colonno, R.J., Lin, P.-F.,Meanwell, N.A., and Kadow, J.F. (2009) Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 5. An evolution from indole to azaindoles leading to the discovery of 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]-pyridin-3-yl)ethane-1,2-dione (BMS-488043), a drug candidate that demonstrates antiviral activity in HIV-1-infected subjects. Journal of Medicinal Chemistry, 52 (23), 7778-7787.
18. De Risi, C., Ferraro, L., Pollini, G.P., Tanganelli, S., Valente, F., and Veronese, A.C. (2008) Efficient synthesis and biological evaluation of two modafinil analogues. Bioorganic and Medicinal Chemistry, 16 (23), 9904-9910.
19. Hadden, M., Goodman, A., Guo, C., Guzzo, P.R., Henderson, A.J., Pattamana, K., Ruenz, M., Sargent, B.J., Swenson, B., Yet, L., Liu, J., He, S., Sebhat, I.K., Lin, L.S., Tamvakopoulos, C., Peng, Q., Kan, Y., Palyha, O., Kelly, M.T., Guan, X.-M., Metzger, J.M., Reitman, M.I., and Nargund, R.P. (2010) Synthesis and SAR of heterocyclic carboxylic acid isosteres based on 2-biarylethylimidazole as bombesin receptor subtype-3 (BRS-3) agonists for the treatment of obesity. Bioorganic & Medicinal Chemistry Letters, 20, 2912-2915.
20. 5 antagonists. Journal of Medicinal Chemistry, 48, 680-693.
21. Arnett, C.D., Wright, J., and Zenker, N. (1978) Synthesis and adrenergic activity of benzimidazole bioisosteres of norepinephrine and isoproterenol. Journal of Medicinal Chemistry, 21 (1), 72-78.
22. Leze, M.-P., Le Borgne, M., Pinson, P., Palusczak, A., Duflos, M., Le Baut, G., and Hartmann, R.W. (2006) Synthesis and biological evaluation of 5-[(aryl)(1Himidazol-1-yl)methyl]-1H-indoles: potent and selective aromatase inhibitors. Bioorganic & Medicinal Chemistry Letters, 16, 1134-1137.
23. Gauthier, J.Y., Chauret, N., Cromlish, W., Desmarais, S., Duong, L.T., Falgueyret, J.-P., Kimmel, D.B., Lamontagne, S., Leger, S., LeRiche, T., Li, C.S., Massé, F., McKay, D.J., Nicoll-Griffith, D.A., Oballa, R.M., Palmer, J.T., Percival, D.J., Riendeau, D., Robichaud, J., Rodan, G.A., Rodan, S.B., Seto, C., Therien, M., Truong, V.-L., Venuti, M.C., Wesolowski, G., Young, R.N.,Zamboni, R., and Black,W.C. (2008) The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K. Bioorganic & Medicinal Chemistry Letters, 18, 923-928.
24. 2-receptor antagonist, cimetidine. Journal ofMedicinal Chemistry, 20 (7), 901-906.
25. Gundisch, D., Kampchen, T., Schwarz, S., Seitz, G., Siegl, J., and Wegge, T. (2002) Syntheses and evaluation of pyridazine and pyrimidine containing bioisosteres of (_)-pyrido[3.4-b]homotropane and pyrido-[3.4-b]tropane as novel nAChR ligands. Bioorganic and Medicinal Chemistry, 10, 1-9.
26. Dodds, E.C., Goldberg, L., Lawson, W., and Robinson, R. (1938) Estrogenic activity of certain synthetic compounds. Nature, 141, 247-248.