Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 16, 2009, Pages 4570-4573

  Mao, Wei wei ^a   Wang, Ting ting ^a,b   Zeng, He ping ^a,b   Wang, Zhi yu ^c   Chen, Jian ping ^c   Shen, Jian gang ^c  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b SOUTH CHINA NORMAL UNIVERSITY   (China)

^c THE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Against breast cancer cell lines; Antiproliferative activity; Breast cancer; Hydroxycoumarin; New substituted 5 hydroxycoumarin; Pyranocoumarin

Indexed keywords

COUMARIN DERIVATIVE; PYRANOCOUMARIN DERIVATIVE; SILICON DIOXIDE; SULFURIC ACID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; SUZUKI REACTION;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CATALYSIS; CELL LINE, TUMOR; COUMARINS; CRYSTALLOGRAPHY, X-RAY; FEMALE; HUMANS; MOLECULAR CONFORMATION; PALLADIUM; PYRANOCOUMARINS; SILICON DIOXIDE;

EID: 67651092267     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.06.098     Document Type: Article

References (30)

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. Rosen S.T. In: Bergan R.C. (Ed). Cancer Chemoprevention Vol. 137 (2001), Academic Publisher, New York
12. Labrie F., Labrie C., Belanger A., Simard J., Gauthier S., Luu-The V., Mérand Y., Giguere V., Candas B., Luo S., Martel C., Singh S.M., Fournier M., Coquet A., Richard V., Charbonneau R., Charpenet G., Tremblay A., Tremblay G., Cusan L., and Veilleux R. J. Steroid Biochem. Mol. Biol. 69 (1999) 51
13. Lacy A., and O'Kennedy R. Curr. Pharm. Des. 10 (2004) 3797
14. Musa M.A., Cooperwood J.S., and Khan M.O.F. Curr. Med. Chem. 15 (2008) 2664
15. Stanchev S., Momekov G., Jensen F., and Manolov I. Eur. J. Med. Chem. 43 (2008) 694
16. Thornes R.D., Daly L., Lynch G., Breslin B., Browne H., Browne H.Y., Corrigan T., Daly P., Edwards G., Gaffney E., Henley J., Healy F., Keane F., Lennon F., McMurray N., O'Loughlin S., Shine M., and Tanner A. J. Cancer Res. Clin. Oncol. 120 (1994) S32
17. Stanway S.J., Purohit A., Woo L.W., Sufi S., Vigushin D., Ward R., Wilson R.H., Stanczyk F.Z., Dobbs N., Kulinskaya E., Elliott M., Potter B.V., Reed M.J., and Coombes R.C. Clin. Cancer Res. 12 (2006) 1585
18. Murray R.d. Fortschr. Chem. Org. Naturst. 83 (2002) 1
19. Houlr J.R.S., and Paya M. Gen. Pharmacol. 27 (1996) 713
20. Carotti A., Carrieri A., Chimichi S., Boccalini M., Cosimelli B., Gnerre C., Carrupt P.A., and Testa B. Bioorg. Med. Chem. Lett. 12 (2002) 3551
21. Alonso M.M., Encío1 I., Martínez-Merino V., Gil M., and Migliaccio M. Br. J. Cancer 85 (2001) 1400
22. Hickson I., Yan Z., Richardson C.J., Green S.J., Martin N.M.B., Orr A.I., Reaper P.M., Jackson S.P., Curtin N.J., and Smith G.C.M. Cancer Res. 64 (2004) 9152
23. Zolfigol M.A. Tetrahedron 57 (2001) 9509
24. Dabiri M., Salehi P., Zolfigol M.A., and Baghbanzadeh M. Heterocycles 71 (2007) 677
25. The crystal structure of 3b and 4b has been registered at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 702721 and 702722, for details of the X-ray structure determination see the Supplementarydata.
26. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
27. Hirano T., Hiromoto K., and Kagechika H. Org. Lett. 9 (2007) 1315
28. Rozhkov R.V., Davisson V.J., and Bergstroma D.E. Adv. Synth. Catal. 350 (2008) 71
29. Chen S., Cho M., Karlsberg K., Zhou D.J., and Yuan Y.C. J. Biol. Chem. 279 (2004) 48071
30. Donnelly A.C., Mays J.R., Burlison J.A., Nelson J.T., Vielhauer G., Holzbeierlein J., and Blagg B.S.J. J. Org. Chem. 73 (2008) 8901