Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 18, 2007, Pages 6119-6125

  Elban, Mark A ^a   Chapuis, Jean C ^b   Li, Mei ^a   Hecht, Sidney M ^a,b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b ARIZONA STATE UNIVERSITY   (United States)

Author keywords

Cepharadiones A and B; Cytotoxicity; Oxoaporphines; Suzuki coupling

Indexed keywords

APORPHINE DERIVATIVE; CEPHARADIONE A; CEPHARADIONE B; DIOXOAPORPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CONTROLLED STUDY; CULTURE MEDIUM; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; EVALUATION; HUMAN; HUMAN CELL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUZUKI REACTION;

ANTINEOPLASTIC AGENTS; APORPHINES; BIOLOGICAL PRODUCTS; CELL SURVIVAL; DRUG EVALUATION, PRECLINICAL; HUMANS; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORPHYRINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34447629723     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.06.035     Document Type: Article

References (29)

1. Hänsel P., and Leuschke A. Phytochemistry 15 (1976) 1323
2. Desai S.J., Prabhu B.R., and Mulchandani N.B. Phytochemistry 27 (1988) 1511-1515
3. Achenbach H., Frey D., and Waibel R. J. Nat. Prod. 54 (1991) 1331-1336
4. Wu T.-S., Ou L.-F., and Teng C.-M. Phytochemistry 36 (1994) 1063-1068
5. Singh S.K., Prasad A.K., Olsen C.E., Jha A., Jain S.C., Parmar V.S., and Wengel J. Phytochemistry 43 (1996) 1355-1360
6. Akusa M., Itokawa H., and Fujita M. Tetrahedron Lett. 15 (1974) 3609-3612
7. Ma J., Jones S.H., Marshall R., Johnson R.K., and Hecht S.M. J. Nat. Prod. 67 (2004) 1162-1164
8. Suau R., López-Romero J.M., Rico R., Alonso F.J., and Lobo C. Tetrahedron 52 (1996) 11307-11320
9. Wijeratne E.M.K., Gunatilaka A.A.L., Kingston D.G.I., Haltiwanger R.C., and Eggleston D.S. Tetrahedron 51 (1995) 7877-7882
10. Woo S.H., Sun N.-J., Cassady J.M., and Snapka R.M. Biochem. Pharmacol. 57 (1999) 1141-1145
11. Zhou B.-N., Johnson R.K., Mattern M.R., Wang X., Hecht S.M., Beck H.T., Ortiz A., and Kingston D.G.I. J. Nat. Prod. 63 (2000) 217-221
12. Gunatilaka A.A.L., Kingston D.G.I., and Johnson R.K. Pure Appl. Chem. 66 (1994) 2219-2222
13. Harrigan G.G., Gunatilaka A.A.L., Kingston D.G.I., Chan G.W., and Johnson R.K. J. Nat. Prod. 57 (1994) 68-73
14. Castedo L., Suau R., and Mouriňo A. Tetrahedron Lett. 17 (1976) 501-502
15. Saá J.M., Mitchell M.J., and Cava M.P. Tetrahedron Lett. 17 (1976) 601-602
16. Kunitomo J.-I., Murakami Y., Oshikata M., Shingu T., Akasu M., Lu S.-T., and Chen I.-S. Phytochemistry 19 (1980) 2735-2739
17. Castedo L., Estévez R., Saá J.M., and Suau R. Tetrahedron Lett. 19 (1978) 2179-2182
18. Estévez J.C., Villaverde M.C., Estévez R.J., and Castedo L. Tetrahedron 50 (1994) 2107-2114
19. Castedo L., Guitián E., Saá J.M., and Suau R. Tetrahedron Lett. 23 (1982) 457-458
20. Atanes N., Castedo L., Guitián E., Saá C., Saá J.M., and Suau R. J. Org. Chem. 56 (1991) 2984-2988
21. Suau R., López-Romero J.M., and Rico R. Tetrahedron Lett. 37 (1996) 9357-9360
22. Suau R., López-Romero J.M., and Rico R. Tetrahedron 53 (1997) 14397-14410
23. Suau R., Rico R., Ortiz-López F.J., López-Romero J.M., Moreno-Maňas M., and Roglans A. Tetrahedron 60 (2004) 5725-5735
24. Miyaura N., Ishiyama T., Sasaki H., Ishikawa M., Satoh M., and Suzuki A. J. Am. Chem. Soc. 111 (1989) 314-321
25. Prévot-Halter I., Smith T.J., and Weiss J. J. Org. Chem. 62 (1997) 2186-2192
26. Albrecht M., and Schneider M. Synthesis (2000) 1557-1560
27. King P.F., and Stroud S.G. Tetrahedron Lett. 26 (1985) 1415-1418
28. Gensler W.J., and Samour C.M. J. Org. Chem. 18 (1953) 9-15
29. Monks A., Scudiero D., Skehan P., Shoemaker R., Paul K., Vestica D., Hose C., Langley J., Cronise P., and Vaigro-Wolf A. J. Natl. Cancer Inst. 83 (1991) 757-766