Synthetic derivatives of the α- and β-amyrin triterpenes and their antinociceptive properties

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 6, 2008, Pages 3377-3386

  Soldi, Cristian ^a   Pizzolatti, Moacir Geraldo ^a   Luiz, Ana Paula ^a   Marcon, Rodrigo ^a   Meotti, Flavia Carla ^a   Mioto, Letícia Adelia ^a   Santos, Adair R S ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Amyrin derivatives; Antinociceptive activity; Structural modifications; Triterpene mixture

Indexed keywords

3 OXO ALPHA AMYRIN; 3 OXO BETA AMYRIN; ACETYLSALICYLIC ACID; ALPHA AMYRIN; ALPHA AMYRIN 2 CAROXYBENZOATE; ALPHA AMYRIN 4 BROMOBENZOATE; ALPHA AMYRIN 4 CHLOROBENZOATE; ALPHA AMYRIN BENZOATE; ALPHA AMYRIN BUTYRATE; ALPHA AMYRIN DECANOATE; ALPHA AMYRIN FORMIATE; ALPHA AMYRIN HEXANOATE; ALPHA AMYRIN OCTANOATE; ALPHA AMYRIN PALMITATE; ALPHA AMYRIN PROPIONATE; BETA AMYRIN; BETA AMYRIN 2 CAROXYBENZOATE; BETA AMYRIN 4 BROMOBENZOATE; BETA AMYRIN 4 CHLOROBENZOATE; BETA AMYRIN BENZOATE; BETA AMYRIN BUTYRATE; BETA AMYRIN DECANOATE; BETA AMYRIN FORMIATE; BETA AMYRIN HEXANOATE; BETA AMYRIN OCTANOATE; BETA AMYRIN PALMITATE; BETA AMYRIN PROPIONATE; MORPHINE; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ABDOMINAL CONSTRICTION; ACYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; INFRARED SPECTROSCOPY; LIGATION; MALE; MOUSE; NOCICEPTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PAIN; STRUCTURE ACTIVITY RELATION;

ANALGESICS; ANIMALS; DISEASE MODELS, ANIMAL; MICE; MOLECULAR STRUCTURE; OLEANOLIC ACID; PAIN; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

EID: 40949087651     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.12.008     Document Type: Article

References (32)

1. Susunaga, G. S. In Estudo químico e biológico da resina produzida pela espécie Protium heptaphyllum March. (Burseraceae). M.Sc Thesis, University of Amazon: Manaus, Brazil, 1996; 155 pp.
2. Ukiva M., Akihisa T., Tokuda H., Suzuki H., Mukainaka T., Ichiishi E., Yasukawa K., Kasahara Y., and Nishino H. Cancer Lett. 177 (2002) 7-12
3. Katerere D.R., Grev A.I., Nash R.J., and Waigh R.D. Phytochemistry 63 (2003) 81-88
4. Oliveira F.A., Lima-Júnior R.C.P., Cordeiro W.M., Vieira-Júnior G.M., Chaves M.H., Almeida F.R.C., Silva R.M., Santos F.A., and Rao V.S.N. Pharmacol. Biochem. Behav. 78 (2004) 719-725
5. Oliveira F.A., Vieira-Junior G.M., Chaves M.H., Almeida F.R.C., Florêncio M.G., Lima-Junior R.C.P., Silva R.M., Santos F.A., and Rao V.S.N. Pharmacol. Res. 49 (2004) 105-111
6. Otuki M.F., Ferreira J., Vieira-Lima F., Silva C.M., Malheiros A., Muller L.A., Cani G.S., Santos A.R.S., Yunes R.A., and Calixto J.B. J. Pharmacol. Exp. Ther. 313 (2005) 310-318
7. Otuki M.F., Vieira-Lima F., Malheiros A., Yunes R.A., and Calixto J.B. Eur. J. Pharmacol. 507 (2005) 253-259
8. Pawar R.S., and Bhutani K.K. Phytomedicine 12 (2005) 391-393
9. Oliveira F.A., Chaves M.H., Almeida F.R.C., Lima Jr. R.C.P., Silva R.M., Maia J.L., Brito G.A.A.C., Santos F.A., and Rao V.S. J. Ethnopharmacol. 98 (2005) 103-108
10. Sun H.X., Zheng Q.F., and Tu J. Bioorg. Med. Chem. 14 (2006) 1189-1198
11. Baltina L.A., Flekhter O.B., Nigmatullina L.R., Boreko E.I., Pavlova N.I., Nikolaeva S.N., Savinova O.V., and Tolstikov G.A. Bioorg. Med. Chem. 13 (2003) 3549-3552
12. Gauthier C., Legault J., Lebrun M., Dufour P., and Pichette A. Bioorg. Med. Chem. 14 (2006) 6713-6725
13. Reyes C.P., Núñez M.J., Jiménez I.A., Busserolles J., Alcaraz M.J., and Bazzocchi I.L. Bioorg. Med. Chem. 14 (2006) 1573-1579
14. Siani A.C., Ramos M.F.S., Lima Jr. O.M., Santos R.R., Ferreira E.F., Soares R.O.A., Rosas E.C., Susunaga G.S., Guimarães A.C., Zoghbi M.G.B., and Henriques M.G.M.O. J. Ethnopharmacol. 66 (1999) 57-69
15. Susunaga G.S., Siani A.C., Pizzolatti M.G., Yunes R.A., and Delle Monache F. Fitoterapia 72 (2001) 709-711
16. Tjolsen A., and Hole K. The Pharmacol. Pain 130/I (1997) 1-20
17. Collier H.O.J., Dinneen J.C., Johnson C.A., and Schneider C. Br. J. Pharmacol. Chemother. 32 (1968) 295-310
18. Koster R., Anderson M., and de Beer E.J. Fed. Proc. (1957) 18-412
19. Vaz Z.R., Cechinel V., Yunes R.A., and Calixto J.B. J. Phamacol. Exp. Ther. 278 (1996) 304-312
20. Hunskaar S., and Hole K. Pain 30 (1987) 103-114
21. Shibata M., Ohkubo T., Takahashi H., and Inuki R. Pain 38 (1989) 347-352
22. Moore P.K., Wallace P., Gaffen Z., Hart S.L., and Babbedge R.C. Br. J. Pharmacol. 110 (1993) 219-224
23. Ribeiro R.A., Vale M.V., Thomazzi S.M., Paschoalato A.B.P., Poole S., Ferreira S.H., and Cunha F.Q. Eur. J. Pharmacol. 387 (2000) 111-118
24. Feng Y., Cui M., and Willis W. Anesthesiology 98 (2003) 729-733
25. Hodgson E., and Levi P. In: Riviere J.E. (Ed). Introduction to Biochemical Toxicology. 2nd ed. (1994), Appleton & Lange, Norwalk, Connecticut, USA 11-48
26. Nogueira C.W., Meotti F.C., Curte E., Pilissão C., Zeni G., and Rocha J.B.T. Toxicology 183 (2003) 29-37
27. Corey E.J., and Suggs J.W. Tetrahedron Lett. 31 (1975) 2647-2650
28. Pinto A.C., Pereira A., Kelecom A., Porreca L., and Ribeiro N. Chem. Pharm. Bull. 36 (1988) 4689-4692
29. Zimmermann M. Pain 16 (1983) 109-110
30. In: Vogel H.G., and Vogel W.H. (Eds). Drug Discovery and Evaluation. Pharmacological Assays (1997), Springer Verlag, Berlin
31. Santos A.R.S., and Calixto J.B. Neuropeptides 31 (1997) 381-389
32. Rodrigues A.L., da Silva G.L., Mateussi A.S., Fernandes E.S., Miguel O.G., Yunes R.A., Calixto J.B., and Santos A.R.S. Life Sci. 70 (2002) 1347-1358