Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities

European Journal of Medicinal Chemistry

Volumn 44, Issue 5, 2009, Pages 2239-2245

  Rao, Gudapati Venkateswara ^a   Swamy, Badrappa Narayana ^a   Chandregowda, Venkateshappa ^a   Reddy, G Chandrasekara ^a  

^a JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Abyssinone; Chalcone; Lipophilicity; MCF 7 cell line; Prenyl; Radical scavenging; Reducing power

Indexed keywords

1 (2,4 DIHYDROXYPHENYL) 3 (2,2 DIMETHYLCHROM 3 ENE 6YL)PROP 2 EN 1 ONE; 1 (2,4 DIHYDROXYPHENYL) 3 (2,2 DIMETHYLCHROMAN 6YL)PROP 2 EN 1 ONE; 1 (2,4 DIHYDROXYPHENYL) 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 (2,4 DIHYDROXYPHENYL) 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (2,4 DIHYDROXYPHENYL) 3 [(4 (3 METHYLBUT 2 ENYL)OXYPHENYL)]PROP 2 EN 1 ONE; 1 (2,4 DIHYDROXYPHENYL) 3 [4 HYDROXY 3 (3 METHYLBUT 2 ENYL)PHENYL]PROP 2 EN 1 ONE; 1 (2,4 DIHYDROXYPHENYL) 3 [4 METHOXY 3 (3 METHYLBUT 2 ENYL)PHENYL]PROP 2 EN 1 ONE; 2 (2',2' DIMETHYL CHROM 3' EN 6' YL) 7 HYDROXYCHROMAN 4 ONE; 2 (2',2' DIMETHYL CHROMAN 6' YL) 7 HYDROXYCHROMAN 4 ONE; 2,2 DIMETHYLCHROM 3 ENE 6 CARBOXALDEHYDE; 2,2 DIMETHYLCHROMAN 6 CARBOXALDEHYDE; 2,4 BIS(METHOXYMETHOXY)ACETOPHENONE; 4 (3 METHYLBUT 2 ENYL)OXYPHENYLBENZALDEHYDE; 4 METHOXY 3 (3 METHYLBUT 2 ENYL)BENZALDEHYDE; 4 METHOXYMETHOXY 3 (3 METHYLBUT 2 ENYL)BENZALDEHYDE; 4 METHOXYMETHOXYBENZALDEHYDE; 7 HYDROXY 2 (4' HYDROXYPHENYL)CHROMAN 4 ONE; 7 HYDROXY 2 (4' METHOXYPHENYL)CHROMAN 4 ONE; 7 HYDROXY 2 [4' HYDROXY 3' (3 METHYLBUT 2 ENYL)PHENYL]CHROMAN 4 ONE; 7 HYDROXY 2 [4' METHOXY 3' (3 METHYLBUT 2 ENYL)PHENYL]CHROMAN 4 ONE; ABYSSINONE 1; ALDEHYDE DERIVATIVE; CHALCONE DERIVATIVE; FLAVANONE DERIVATIVE; UNCLASSIFIED DRUG; ABYSSINONE I; ACETOPHENONE DERIVATIVE; ALDEHYDE; ANTINEOPLASTIC AGENT; ANTIOXIDANT; FLAVONOID; RESACETOPHENONE; RESORCINOL DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL STRAIN MCF 7; CYCLIZATION; CYTOTOXICITY; DEPROTECTION REACTION; DRUG SYNTHESIS; PRENYLATION; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ACETOPHENONES; ALDEHYDES; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHALCONES; FLAVONOIDS; HUMANS; PRENYLATION; RESORCINOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 62749083678     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.05.032     Document Type: Article

References (28)

1. Abeza B.M., Nagadjui B.T., Dongo E., Nagameni B., Nindi M., and Bezabih M. Phytochemistry 59 (2002) 877-883
2. Sutthivaiyakit S., Ungnont S., Sutthivaiyakit P., and Suchsamrarn A. Tetrahedron 58 (2002) 3619-3622
3. Cidada H.M., Nacimento M.S., Pinto M.M.M., Kijjoa A., Silva A.M.S., and Herz W. Planta Med. 67 (2001) 867-870
4. Meragelman K.M., Mckee T.C., and Boyd M.R. J. Nat. Prod. 64 (2001) 546-548
5. Dufall K.G., Ngadjui B.T., Simeon K.F., Abegaz B.M., and Croft K.D. J. Ethnopharmacol. 87 (2003) 67-72
6. Jang D.S., Cuendet M., Hawthorne M., Kardono L.B., Kawanishi K., Fong H.H.S., Metha R.G., Pezzuto J.M., and Kinghorn A.D. Phytochemistry 61 (2002) 867-872
7. Yamahara J., Mochizuki M., Chisaka T., Fujimora H., and Tamai Y. Chem. Pharm. Bull. 38 (1990) 1039
8. Tahara S., Nakahara S., Mizutani J., and Ingham J.L. Agric. Biol. Chem. 48 (1984) 1471-1477
9. Di Pietro A., Conseil G., Perez-Victoria J.M., Dayan G., Baubichon-Cortay H., and Trompier D. Cell Mol. Life Sci. 59 (2002) 307-322
10. Conseil G., Baubichon-Cortay H., Dayan G., Jault J.M., D.Barron, and Di Pietro A. Proc. Natl. Acad. Sci. U S A 95 (1998) 9831-9836
11. Tchamo D.N., Dijoux-France M.G., Mariotte A.M., Tsamo E., Daskiewicz J.B., Bayet C., Barron G., Conseil G., and Di Pietro A. Bioorg. Chem. Lett. 10 (2000) 1343-1345
12. Comte G., Daskiewicz J.B., Bayet C., Conseil G., Viornery-Vanier A., Dumontet C., Di Pietro A., and Barron D. J. Med. Chem. 44 (2001) 763-768
13. Barron D., and Ibraham R.K. Phytochemistry 43 (1996) 921-982
14. Barron D., Balland C., Possety F., Ravanel P., and Desfougeres A. Acta Bot. Gall. 143 (1996) 509
15. Botta B., Vitali A., Menendez P., Misiti D., and Monache G.D. Curr. Med. Chem. 12 (2005) 713-768
16. Kamat V.S., Chuo F.Y., Kubo I., and Nakanishi K. Heterocycles 15 (1981) 1163-1170
17. Kokwaro J.O. Medicinal Plants of East Africa (1976), East African Literature Bureau, Nairobi
18. Taniguchi M., Chapya A., Kubo I., and Nakauishi K. Chem. Pharm. Bull. 26 (1978) 2910-2916
19. Kinghorn A.D., Su B.N., Jang D.S., Chang L.C., Lee D., Gu J.Q., Carcache-Blanco E.J., Pawlus A.D., Lee S.K., Park E.J., Cuendet M., Gills J.J., Bhat K., Park H.S., Greenwood E.M., Song L.L., Jang M., and Pezzuto J.M. Planta Med. 70 (2004) 691-705
20. A.D. Kinghorn, J.M. Pezzuto, D. Lee, K.P.L. Bhat. US patent, 2003, 0,125,377.
21. Moriarty R.M., Grubjesic S., Surve B.C., Chandrasekara S.N., Prakash O., and Naithani R. Eur. J. Med. Chem. 41 (2006) 263-267
22. Bigi F., Casiraghi G., Casnati G., and Satori G. Synthesis (1981) 310-312
23. Gliisenkamp K.H., and Buchi G. J. Org. Chem. 51 (1986) 4481-4483
24. Maiti A., Cuendet M., Croy V.L., Endringer D.C., Pezzuto J.M., and Cushman M. J. Med. Chem. 50 (2007) 2799-2806
25. Blois M.S. Nature 181 (1958) 1199-2000
26. Oyaizu M. Jpn. J. Nutr. 44 (1986) 307-315
27. Miranda C.L., Steven J.F., Ivanov V., McCall M., Frei B., Deinzer M.L., and Buhler D.L. J. Agric. Food Chem. 48 (2000) 3876
28. Mossman T. J. Immunol. Methods. 65 (1983) 55-63