Antitumor agents 243. Syntheses and cytotoxicity of desmosdumotin C derivatives

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 6, 2005, Pages 2325-2330

  Nakagawa Goto, Kyoko ^a   Wu, Jiu Hong ^b   Bastow, Kenneth F ^a   Wu, Chin Chung ^a   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b 306 HOSPITAL OF PLA   (China)

Author keywords

Antitumor; Cytotoxicity; Desmosdumotin C analogs

Indexed keywords

2 (1' HYDROXY 3' THIOPHEN 2'' YLALLYLIDENE) 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 2 (3' FURAN 2'' YL 1' HYDROXYALLYLIDENE) 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 2 [(1' HYDROXY 3' THIAZOL 2 YLALLYLIDENE) 5 METHOXY 4,6,6 TRIMETHYL 1,3 CYCLOHEX 4 ENE 1,3 DIONE; 2 [1 HYDROXY 3 (2 METHOXYPHENYL)ALLYLIDENE] 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 2 [1 HYDROXY 3 (3 METHOXYPHENYL)ALLYLIDENE] 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 2 [1 HYDROXY 3 (4 BROMOPHENYL)ALLYLIDENE] 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 2 [1 HYDROXY 3 (4 HYDROXYPHENYL)ALLYLIDENE] 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 2 [1 HYDROXY 3 (4 METHOXYPHENYL)ALLYLIDENE] 5 METHOXY 4,6,6 TRIMETHYLCYCLOHEX 4 ENE 1,3 DIONE; 5 HYDROXY 2,2,6,6 TETRAMETHYL 4 (3 PHENYLACRYLOYL)CYCLOHEX 4 ENE 1,3 DIONE; ANTINEOPLASTIC AGENT; AROMATIC COMPOUND; DESMOSDUMOTIN C; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; TUMOR CELL; TUMOR CELL LINE;

EID: 13844313223     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.12.040     Document Type: Article

References (25)

1. Chung Yao Da Tzu Dien (Dictionary of Chinese Materia Medicia); Jiang Su New Medical College, Ed.; Shanghai Science & Technology: Hong Kong, 1977; Vol. 2, p 1919
2. J. Onodera, H. Obara, R. Hirose, S. Matsuba, N. Sato, S. Sato, and M. Suzuki Chem. Lett. 1989 1571 1574
3. S. Sato, H. Obara, J. Onodera, A. Endo, and S. Matsuba Bull. Chem. Soc. Jpn. 65 1992 452 457
4. M. Nishizawa, H. Yamada, J. Sano, S. Ito, Y. Hayashi, H. Ikeda, M. Shiro, and H. Tokuda Tetrahedron Lett. 32 1991 211 212
5. S. Sato, H. Obara, A. Endo, J. Onodera, and S. Matsuba Bull. Chem. Soc. Jpn. 65 1992 2552 2554
6. T. Meikle, and R. Stevens J. Chem. Soc. Perkin Trans. 1 11 1978 1303 1312
7. J.H. Wu, A.T. McPhail, K.F. Bastow, H. Shiraki, J. Ito, and K.H. Lee Tetrahedron Lett. 43 2002 1391
8. Scifinder literature search
9. Nakagawa-Goto, K.; Wu, J. H.; Lee, K. H. Syn. Commun., in press
10. M. Nilsson Acta Chem. Scand. 13 1959 750
11. G. Nowy, W. Riedl, and H. Simon Chem. Ber. 99 1966 2975
12. W. Riedl, J. Nickl, K.H. Risse, and R. Mitteldorf Chem. Ber. 89 1956 1849
13. P.A. Marchand, D.M. Weller, and R.F. Bonsall J. Agric. Food. Chem. 48 2000 1882
14. S. Sato, H. Obara, A. Endo, J. Onodera, and S. Matsuba Bull. Chem. Soc. Jpn. 65 1992 2552
15. H. Obara, J. Onodera, S. Abe, and T. Saito Bull. Chem. Soc. Jpn. 53 1980 289
16. H. Obara, J. Onodera, and F. Shirasaki Chem. Lett. 1980 1095
17. S. Forsen, and M. Nilsson Acta Chem. Scand. 13 1959 1383
18. S. Forsen, M. Nilsson, and C.A. Wachtmeister Acta Chem. Scand. 16 1962 583
19. I.R.C. Bick, and D.H.S. Horn Aust. J. Chem. 18 1965 1405
20. P.M. Sbit, L. Dupont, and O. Dideberg Acta Cryst. C43 1987 2204
21. C. Vilain, A. Hubert, L. Dupont, K.R. Markham, and E. Wollenweber J. Biosci. 42 1987 849
22. The enolic form b with extended conjugated bonds could be preferred over form c with cross-conjugated bonds. This postulate has been discussed using NMR in the following paper I.R.C. Bick, and D.H.S. Horn Aust. J. Chem. 18 1965 1405
23. L.V. Rubinstein, R.H. Shoemaker, K.D. Paull, R.M. Simo, S. Tosini, P. Skehan, P.A. Scudiero, A. Monks, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1113
24. P.J. Ferguson, M.H. Fisher, J. Stephenson, D.H. Li, B.S. Zhou, and Y.C. Cheng Cancer Res. 48 1988 5956
25. D.R. Beidler, J.Y. Chang, B.S. Zhou, and Y.C. Cheng Cancer Res. 56 1996 345