Synthesis and biological evaluation of 3,4,6-triaryl-2-pyranones as a potential new class of anti-breast cancer agents

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 11, 2009, Pages 3847-3856

  Shankar, Ravi ^a   Chakravarti, Bandana ^a   Singh, Uma Sharan ^a   Ansari, Mohd Imran ^a   Deshpande, Shreekant ^a   Dwivedi, Shailendra Kumar Dhar ^a   Bid, Hemant Kumar ^a   Konwar, Rituraj ^a   Kharkwal, Geetika ^a   Chandra, Vishal ^a   Dwivedi, Anila ^a   Hajela, K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Anti proliferative; Apotosis; DNA fragmentation; Triaryl 2 pyranones

Indexed keywords

3,4 BIS(4 HYDROXYPHENYL) 6 PHENYLPYRAN 2 ONE; 4,6 BIS(4 HYDROXYPHENYL) 3 PHENYLPYRAN 2 ONE; 4,6 BIS(4 METHOXYPHENYL) 3 PHENYLPYRAN 2 ONE; 6 (4 HYDROXYPHENYL) 3,4 DIPHENYLPYRAN 2 ONE; ANTINEOPLASTIC AGENT; BENZENE; BENZENE DERIVATIVE; CASPASE; DNA FRAGMENT; ESTRADIOL; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ETHYLENE DERIVATIVE; ETOPOSIDE; PHENOL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAN DERIVATIVE; TAMOXIFEN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; FEMALE; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERIDINES; PYRONES; PYRROLIDINES;

EID: 65549108714     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.032     Document Type: Article

References (31)

1. Rosen S.T. In: Bergan R.C. (Ed). Cancer Chemoprevention (2001), Academic, New York 137
2. 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
3. Jorden V.C., and Gradishar W.J. Mol. Aspect Med. 18 (1997) 187
4. Lerner L.J., and Jordan V.C. Cancer Res. 50 (1990) 4177
5. Jorden V.C. J. Steroid Biochem. Mol. Biol. 74 (2000) 269
6. Rosati R.L., Da Silva Jardine P., Cameron K.O., Thompson D.D., Ke H.Z., Toler S.M., Brown T.A., Pan L.C., Ebbinghaus C.F., Reinhold A.R., Elliott N.C., Newhouse B.N., Tjoa C.M., Sweetnam P.M., Cole M.J., Arriola M.W., Gauthier J.W., Crawford D.T., Nickerson D.F., Pierie C.M., Qi H., Simmons H.A., and Tkalcevic G.T. J. Med. Chem. 41 (1998) 2928
7. Saeed A., Sharma A.P., Durani N., Jain R., Durani S., and Kapil R.S. J. Med. Chem. 33 (1990) 3210
8. Gauither S., Caron B., Cloutier J., Dory Y.L., Favre A., Larouche D., Mailhot J., Quellet C., Schwerdtfeger A., Leblanc G., Martel C., Simard J., Merand Y., Belanger A., Labrie C., and Labrie F. J. Med. Chem. 40 (1997) 2117
9. Brady H., Desai I., Gayo-Fung L.M., Khammungkhune S., McKie J., O'Leary E., Pascasio L., Sutherland M.K., Anderson D.W., Bhagwat S.S., and Stein B. Cancer Res. 62 (2002) 1439
10. Gottardis M.M., and Jordan V.C. Cancer Res. 47 (1987) 4020
11. Mchlacken G.P., and Fairlamb J.S. Nat. Prod. Rep. 22 (2005) 369
12. Barrero A.F., Oltra J.E., Herrador M.M., Sanchez J.F., Quilez J.F., Rojas F.J., and Reyes J.F. Tetrahedron 49 (1993) 141
13. Marrision L.R., Dickinson J.M., and Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12 (2002) 3509
14. Fairlamb I.J.S., Marrison L.R., Dickinson J.M., Lu F., and Schmidt J.P. Bioorg. Med. Chem. 12 (2004) 4285
15. Schlingmann G., Milne L., and Carter G.T. Tetrahedron 54 (1998) 13013
16. Dickinson J. Nat. Prod. Rep. 10 (1993) 71
17. VaraPrasad J.V.N., Para K.S., Lunney E.A., Ortwine D.F., Dunbar J.B., Ferguson D., Tummino P.J., Hupe D., Tait B.D., Domagala J.M., Humbelet C., Bhat T.N., Liu B., Guerin D.A.M., Baldwin E.T., Erickson J.W., and Sawyer T.K. J. Am. Chem. Soc. 116 (1994) 6989
18. Clercq E.D. J. Med. Chem. 38 (1995) 2491
19. Romines K.R., and Thaisrivongs S. Drugs Future 20 (1995) 377
20. Rao P.N.P., Amini M., Li H., Habeeb A.G., and Knaus E.E. J. Med. Chem. 46 (2003) 4872
21. Singh M.M. Med. Res. Rev. 21 (2001) 302
22. Minutdo F., Bertini S., Papi C., Carlson K.E., Katzenellenbogen J.A., and Macchit M. J. Med. Chem. 44 (2001) 4288
23. Stauffer S.R., Huang Y.R., Aron Z.D., Coletta C.J., Sun J., Katzenellenbogen B.S., and Katzenellenbogen J.A. Bioorg. Med. Chem. 9 (2001) 151
24. Kim Y.W., Mobley J.A., and Brueggemeier R.W. Bioorg. Med. Chem. Lett. 13 (2003) 1475
25. Jiang B., and Si Y.G. Tetrahedron Lett. 43 (2002) 8323
26. Rao P.N.P., Uddin M.J., and Knaus E.E. J. Med. Chem. 47 (2004) 3972
27. Chowdhury C., and Kundu N.G. Tetrahedron Lett. 37 (1996) 7323
28. Baddar F.G., Al-Hajjar F.H., and El-Rayyes N.R. J. Heterocyl. Chem. 13 (1976) 195
29. Mosmann T. J Immunol Methods 65 (1983) 55
30. Chattopadhyay N., Yano S., Tfelt-Hansen J., Rooney P., Kanuparthi D., Bandyopadhyay S., Ren X., Terwilliger E., and Brown E.M. Endocrinology 145 (2004) 3451
31. Sashidhara K.V., Rosaiah J.N., Kumar A., Bid H.K., Konwar R., and Chattopadhyay N. Phytother. Res. 21 (2007) 1105