Synthesis and evaluation of a novel series of heterocyclic oleanolic acid derivatives with anti-osteoclast formation activity

European Journal of Medicinal Chemistry

Volumn 44, Issue 7, 2009, Pages 2796-2806

  Li, Jun Feng ^a   Zhao, Yu ^a   Cai, Min Min ^a   Li, Xiao Fei ^a   Li, Jian Xin ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Heterocyclic derivatives; Inhibitory activity; Oleanolic acid; Osteoclast formation; SAR

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; INDOLE DERIVATIVE; OLEANOLIC ACID DERIVATIVE; PYRAZINE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOXALINE DERIVATIVE;

ACHYRANTHES; ANIMAL CELL; ARTICLE; CELL MATURATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; MOUSE; NONHUMAN; OSTEOCLAST; OSTEOLYSIS; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; ANIMALS; CELL SURVIVAL; DRUG DESIGN; HETEROCYCLIC COMPOUNDS; MALE; MICE; OLEANOLIC ACID; OSTEOCLASTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 65349156244     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.12.024     Document Type: Article

References (25)

1. Epstein S. Clin. Ther. 28 (2006) 151-173
2. Reginster J.Y., and Burlet N. Bone 38 (2006) 4-9
3. Johnell O., and Kanis J.A. Osteoporosis Int. 17 (2006) 1726-1733
4. Farina C., and Gagliardi S. Curr. Pharm. Des. 8 (2002) 2033-2048
5. Li J.X., Hareyama T., Tezuka Y., Zhang Y., Miyahara T., and Kadota S. Planta Med. 71 (2005) 673-679
6. Zhang Y., Li J.X., Zhao J.W., Wang S.Z., Pan Y., Tanaka K., and Kadota S. Bioorg. Med. Chem. Lett. 15 (2005) 1629-1632
7. Giner-Larza E.M., Manez S., Recio M.C., Giner R.M., Prieto J.M., Cerda-Nicolas M., and Rios J.L. Eur. J. Pharmacol. 428 (2001) 137-143
8. Hsu H.Y., Yang J.J., and Lin C.C. Cancer Lett. 111 (1997) 7-13
9. Jeong H.G. Toxicol. Lett. 105 (1999) 215-222
10. Inglis S., Jones R., Fritz D., Stojkoski C., Booker G., and Pyke S. Org. Biomol. Chem. 3 (2005) 2543-2557
11. Tavares F.X., Deaton D.N., Miller L.R., and Wright L.L. J. Med. Chem. 47 (2004) 5057-5068
12. Tavares F.X., Deaton D.N., Miller A.B., Miller L.R., Wright L.L., and Zhou H.Q. J. Med. Chem. 47 (2004) 5049-5056
13. Jeong H.J., Chai H.B., Park S.Y., and Kim D.S.H.L. Bioorg. Med. Chem. Lett. 9 (1999) 1201-1204
14. Honda T., Finlay H.J., Gribble G.W., Suh N., and Sporn M.B. Bioorg. Med. Chem. Lett. 7 (1997) 1623-1628
15. Finlay H.J., Honda T., and Gribble G.W. ARKIVOC 7 (2002) 38-46
16. Urban M., Sarek J., Kvasnica M., Tislerova I., and Hajduch M. J. Nat. Prod. 70 (2007) 526-532
17. Thummel R.P., Chirayil S., Hery C., Lim J.L., and Wang T.L. J. Org. Chem. 58 (1993) 1666-1671
18. Liesch J.M., McMillan J.A., Pandey R.C., Paul Jr. I.C., and Rinehart K.L. J. Am. Chem. Soc. 98 (1976) 300-301
19. Brenner M., and Huber W. Helv. Chim. Acta 36 (1953) 1109-1115
20. Sanders J.M., Song Y.C., Chan J.M.W., Zhang J.H., Jennings S., Kosztowski T., Odeh S., Flessner R., Schwerdtfeger C., Kotsikorou E., Meints G.A., Gomez A.O., Gonzalez-Pacanowska D., Raker A.M., Wang H., van Beek E.R., Papapoulos S.E., Morita C.T., and Oldfield E. J. Med. Chem. 48 (2005) 2957-2963
21. Widler L., Jaeggi K.A., Glatt M., Muller K., Bachmann R., Bisping M., Born A.R., Cortesi R., Guiglia G., Jeker H., Klein R., Ramseier U., Schmid J., Schreiber G., Seltenmeyer Y., and Green J.R. J. Med. Chem. 45 (2002) 3721-3738
22. Takahashi N., Akatsu T., Udagawa N., Sasaki T., Yamaguchi A., Moseley J.M., Martin T.J., and Suda T. Endocrinology 123 (1988) 2600-2602
23. Reid D.M., Hosking D., Kendler D., Brandi M.L., Wark J.D., Marques-Neto J.F., Weryha G., Verbruggen N., Hustad C.M., Mahlis E.M., and Melton M.E. Int. J. Clin. Pract. 62 (2008) 575-584
24. Notoya K., Yoshida K., Taketomi S., Yamazaki I., and Kumegawa M. Calcif. Tissue Int. 53 (1993) 206-209
25. Makhija M.T., Kasliwal R.T., Kulkarni V.M., and Neamati N. Bioorg. Med. Chem. 12 (2004) 2317-2333