Synthesis of novel curcumin analogues and their evaluation as selective cyclooxygenase-1 (COX-1) inhibitors

Chemical and Pharmaceutical Bulletin

Volumn 55, Issue 1, 2007, Pages 64-71

  Handler, Norbert ^a   Jaeger, Walter ^a   Puschacher, Helmut ^a   Leisser, Klaus ^a   Erker, Thomas ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Cancer; Curcumin; Cyclooxygenase 1; Cyclooxygenase 2

Indexed keywords

1,11 BIS(4 METHOXYPHENYL) 1,3,8,10 UNDECATETRAEN 5,7 DIONE; 1,7 BIS(2,3,4 TRIMETHOXYPHENYL) 1,6 HEPTADIEN 3,5 DIONE; 1,7 BIS(3,4 DIFLUOROPHENYL) 1,6 HEPTADIEN 3,5 DIONE; 1,7 BIS[4 (METHYLMERCAPTO)PHENYL] 1,6 HEPTADIEN 3,5 DIONE; 1,7 BIS[4 (METHYLSULFONYL)PHENYL] 1,6 HEPTADIEN 3,5 DIONE; 1,7 DIFERROCENYL 1,6 HEPTADIEN 3,5 DIONE; CELECOXIB; CURCUMIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2; INDOMETACIN; METHYL 4[7(4 METHOXYCARBONYL)PHENYL] 3,5 DIOXO 1,6 HEPTADIENYLBENZOIC ACID; PROSTAGLANDIN E2; UNCLASSIFIED DRUG;

ARTICLE; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY;

CURCUMIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE INHIBITORS; DRUG EVALUATION, PRECLINICAL; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33846034078     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.64     Document Type: Article

References (21)

1. Weber W. M., Hunsaker L. A., Roybal C. N., Bobrovnikova-Marjon E. V., Abcouwer S. F., Royer R. E., Deck L. M., Vander Jagt D. L., Bioorg. Med. Chem., 14, 2450-2461 (2006).
2. Hong J., Bose M., Ju J., Ryu J., Chen X., Sang S., Lee M., Yang C., Carcinogenesis, 25, 1671-1679 (2004).
3. Woo H. B., Shin W., Lee S., Ahn C. M., Biorg. Med. Chem. Lett., 15, 3782-3786 (2005).
4. Venkateswarlu S., Ramachandra M. S., Subbaraju G. V., Bioorg. Med. Chem., 13, 6374-6380 (2005).
5. Goel A., Boland C. R., Chauhan D. P., Cancer Lett., 172, 111-118 (2001).
6. Lev-Ari S., Strier L., Kazanov D., Madar-Shapiro L., Dvory-Sobol H., Pinchuk I., Marian B., Lichtenberg D., Arber N., Clin. Cancer Res., 11, 6738-6744 (2005).
7. Nurfina A. N., Reksohadiprodjo M. S., Timmermann H., Jenie U. A., Sugiyanto D., van der Goot H., Eur. J. Med. Chem., 32, 321-328 (1997).
8. Joe B., Vijaykamur N., Lokesh B. R., Crit. Rev. Food Sci. Nutr., 44, 97-111 (2004).
9. Xie W. L., Chipman J. G., Robertson D. L., Erikson R. L., Simmons D. L., Proc. Natl. Acad. Sci. U.S.A., 88, 2692-2696 (1991).
10. Fournier D. B., Gordon G. B., J. Cell Biochem. Suppl., 34, 97-102 (2000).
11. Onn A., Tseng J. E., Herbst R. S., Clin. Cancer Res., 7, 3311-3313 (2001).
12. Kitamura T., Itoh M., Noda T., Matsuura M., Wakabayashi K., Int. J. Cancer, 109, 576-580 (2004).
13. Sano H., Noguchi T., Miyajima A., Hashimoto Y., Miyachi H., Bioorg. Med. Chem. Lett., 16, 3068-3072 (2006).
14. Gupta R. A., Tejada L. V., Tong B. J., Das S. K., Morrow J. D., Dey S. K., DuBois R. N., Cancer Res., 63, 906-911 (2003).
15. Mazumder A., Neamati N., Sunder S., Schulz J., Pertz H., Eich E., Pommier Y., J. Med. Chem., 40, 3057-3063 (1997).
16. Pabon H. J. J., Rec. Trav. Chim. Pays-Bas, 83, 379-386 (1964).
17. Selvam C., Jachak S. M., Thilagavathi R., Chakraborti A. K., Bioorg. Med. Chem. Lett., 15, 1793-1797 (2005).
18. Abloa E. E., Bernstein F. C., Bryant S. H., Koetzle T. F., Weng J., "Protein Data Bank in Crystallographic Databases-Information Content, Software Systems, Scientific Applications," ed. by Allen F. H., Berjerhoff G., Sievers R., Data Commision of the International Union of Crystallography, Bonn, 1987, p. 171.
19. Kurumbail R. G., Stevens A. M., Gierse J. K., McDonald J. J., Stegeman R. A., Pak J. Y., Gildehaus D., Miyashiro J. M., Penning T. D., Seibert K., Isakson P. C., Stallings W. C., Nature (London), 384, 644-648 (1996).
20. Loll P. J., Picot D., Ekabo O., Garavito R. M., Biochemistry, 35, 7330-7340 (1996).
21. Riendeau D., Percival M. D., Boyce S., Brideau C., Charleson S., Cromlish W., Ethier D., Evans J., Falgueyret J.-P., Ford-Hutchinson A. W., Gordon R., Greig G., Gresser M., Guay J., Kargman S., Leger S., Mancini J. A., O'Neill G., Ouellet M., Rodger I. W., Therien M., Wang Z., Webb J. K., Wong E., Chan C. C., Brit. J. Pharmacol., 121, 105-117 (1997).