Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 6, 2007, Pages 2269-2282

  Jacquot, Yves ^a,b   Laïos, Ioanna ^c   Cleeren, Anny ^c   Nonclercq, Denis ^d   Bermont, Laurent ^e,f   Refouvelet, Bernard ^a   Boubekeur, Kamal ^b   Xicluna, Alain ^a   Leclercq, Guy ^c   Laurent, Guy ^d  

^a UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^b SORBONNE UNIVERSITÉ   (France)

^c JULES BORDET INSTITUTE   (Belgium)

^d UNIVERSITY OF MONS   (Belgium)

^e UNIVERSITY HOSPITAL JEAN MINJOZ   (France)

^f IFR 133   (France)

Author keywords

4 Aminocoumarins; Breast cancer cells; Estrogenic activity

Indexed keywords

4 CYCLOHEXYLAMINO 3 (2 METHYLBENZYL)COUMARIN; 4 CYCLOPENTYLAMINO 3 (2 METHYLBENZYL)COUMARIN; 4 N DODECYLAMINO 3 (2 METHYLBENZYL)COUMARIN; 4 PHENYLETHYLAMINO 3 (2 METHYLBENZYL)COUMARIN; 7 METHOXY 4 N PENTYLAMINO 3 (2 METHYLBENZYL)COUMARIN; ANTIESTROGEN; COUMARIN DERIVATIVE; ESTRADIOL; ESTROGEN RECEPTOR; FULVESTRANT; TRITIUM; UNCLASSIFIED DRUG;

ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; CANCER GROWTH; CELL PROLIFERATION; CELL STIMULATION; CELL STRAIN MCF 7; CONTROLLED STUDY; DOWN REGULATION; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ESTROGEN ACTIVITY; HUMAN; HUMAN CELL; MITOGENESIS; PLASMID; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; TRANSACTIVATION;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL PROLIFERATION; COUMARINS; ESTROGENS; HUMANS; LIGANDS; LUCIFERASES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROMOTER REGIONS (GENETICS); RECEPTORS, ESTROGEN; THYMIDINE KINASE; TRANS-ACTIVATION (GENETICS); TRANSCRIPTION, GENETIC; TUMOR CELLS, CULTURED;

EID: 33846979462     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.01.025     Document Type: Article

References (44)

1. Bravic G., Gaultier J., and Hauw C. C.R. Acad. Sci. Paris 267 (1968) 1790
2. McEvoy M.T., and Stern R.S. Pharmacol. Ther. 34 (1987) 75
3. Nettleton D.E. Drugs Future 34 (1996) 1257
4. Hoeksema H., Caron E.L., and Hinman J.W. J. Am. Chem. Soc. 78 (1956) 2019
5. Refouvelet B., Guyon C., Jacquot Y., Girard C., Fein H., Bévalot F., Robert J.-F., Heyd B., Mantion G., Richert L., and Xicluna A. Eur. J. Med. Chem. 39 (2004) 931
6. Taniguchi M., Xiao Y.-Q., Liu X.-H., Yabu A., Hada Y., Guo L.-Q., Yamazoe Y., and Baba K. Chem. Pharm. Bull. 47 (1999) 713
7. Livingston A.L., Bickoff E.M., Lundin R.E., and Jurd L. Tetrahedron 20 (1964) 1963
8. Jacquot Y., Rojaz C., Refouvelet B., Robert J.-F., Leclercq G., and Xicluna A. Mini-Rev. Med. Chem. 3 (2003) 387
9. Roelens F., Huvaere K., Dhooge W., van Cleemput M., Comhaire F., and De Keukeleire D. Eur. J. Med. Chem. 40 (2005) 1042
10. Noeldner M., Hauer H., and Chatterjee S.S. Drugs Future 21 (1996) 779
11. Usui T. Endocrine J. 53 (2006) 7
12. Jacquot Y., Refouvelet B., Bermont L., Adessi G.L., Leclercq G., and Xicluna A. Pharmazie 57 (2002) 233
13. Jacquot Y., Bermont L., Giorgi H., Refouvelet B., Adessi G.L., Daubrosse E., and Xicluna A. Eur. J. Med. Chem. 36 (2001) 127
14. Jacquot Y., Cleeren A., Laios I., Ma Y., Boulhadour A., Bermont L., Refouvelet B., Adessi G., Leclercq G., and Xicluna A. Biol. Pharm. Bull. 25 (2002) 335
15. Tabakovic K., Tabakovic I., Ajdini N., and Leci O. Synthesis (1987) 308
16. Ivanov I.C., Karagiosov S.K., and Manolov I. Arch. Pharm. (Weinheim) 324 (1991) 61
17. Vanhaelen M., and Vanhaelen-Fastre R. Pharm. Acta Helv. 51 (1976) 307
18. Traven F.V., Negrebetsky V.V., Vorobjeva L.I., and Carberry E.A. Can. J. Med. 75 (1997) 377
19. Traven F.V., Manaev A.V., Safronova O.B., and Chibisova T.A. J. Elec. Spectrosc. Relat. Phenom. 122 (2002) 47
20. Schroeder C.H., Titus E.D., and Link K.P. J. Am. Chem. Soc. 79 (1957) 3291
21. Cremer D., and Pople J.A. J. Am. Chem. Soc. 95 (1975) 1354
22. Anstead G.M., Carlson K.E., and Katzenellenbogen J.A. Steroids 62 (1997) 268
23. Tedesco R., Katzenellenbogen J.A., and Napolitano E. Bioorg. Med. Chem. Lett. 7 (1997) 2919
24. Jin L., Borrás M., Lacroix M., Legros N., and Leclercq G. Steroids 60 (1995) 512
25. El-Khissiin A., and Leclercq G. FEBS Lett. 448 (1999) 160
26. Laïos I., Journé F., Nonclercq D., Vidal D.S., Toillon R.-A., Laurent G., and Leclercq G. J. Steroid Biochem. Mol. Biol. 94 (2005) 347
27. Journé F., Body J.-J., Leclercq G., Nonclercq D., and Laurent G. Breast Cancer Res. Treat. 86 (2004) 39
28. Nonclercq D., Journé F., Body J.-J., Leclercq G., and Laurent G. Mol. Cell. Endocrinol. 227 (2004) 53
29. Wijayaratne A.L., and McDonnell D.P. J. Biol. Chem. 143 (2002) 35684
30. Blazejewski J.-C., Wilmshurst M.P., Popkin M.D., Wakselman C., Laurent G., Nonclercq D., Cleeren A., Ma Y., Seo H.-S., and Leclercq G. Bioorg. Med. Chem. 11 (2003) 335
31. Kekenes-Huskey P.M., Muegge I., von Rauch M., Gust R., and Knapp E.-W. Bioorg. Med. Chem. 12 (2004) 6527
32. Lonard D.M., Nawaz Z., Smith C.L., and O'Malley B.W. Mol. Cell 5 (2000) 939
33. Alarid E.T., Preisler-Mashek M., and Solodin N.M. Endocrinology 144 (2003) 3469
34. Fan M., Park A., and Nephew K.P. Mol. Endocrinol. 19 (2005) 2901
35. van Hoorn W.P. J. Med. Chem. 45 (2002) 584
36. Wang Y., Chirgadze N.Y., Briggs S.L., Khan S., Jensen E.V., and Burris T.P. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 9908
37. Rodriguez A.L., Tamrazi A., Collins M.L., and Katzenellenbogen J.A. J. Med. Chem. 47 (2004) 600
38. Blessing R.H. Acta Cryst. A51 (1995) 33
39. Sheldrick G.M. SHELXS-86, Computer Program for Structure Solution (1986), University of Gottingen, Germany
40. Sheldrick G.M. SHELXL-97, Computer Program for Structure Refinement (1997), University of Gottingen, Germany
41. Brandenburg K., and Berndt M. Diamond™ (1999), Crystal Impact GbR, Bonn, Germany
42. Journé F., Chaboteaux C., Dumon J.-C., Leclercq G., Laurent G., and Body J.-J. Br. J. Cancer 91 (2004) 1703
43. Pons M., Cagne D., Nicolas J.C., and Mehtali M. Biotechniques 9 (1990) 450
44. Demirpence E., Duchesne M.J., Badia E., Gagne D., and Pons M. J. Steroid Biochem. Mol. Biol. 46 (1993) 355