The structure of a coumarin derivative related to the carcinogen benz[a]anthracene

Carcinogenesis

Volumn 17, Issue 10, 1996, Pages 2245-2248

  Flocco, Maria M ^a,c   Carrell, H L ^a   Harvey, Ronald G ^b   Zacharias, David E ^a   Glusker, Jenny P ^a  

^a FOX CHASE CANCER CENTER   (United States)

^b UNIVERSITY OF CHICAGO   (United States)

^c KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BENZ[A]ANTHRACENE; CARBONYL DERIVATIVE; CARCINOGEN; COUMARIN DERIVATIVE; HYDROGEN; METHYL GROUP; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; ELECTRON TRANSPORT; HYDROPHOBICITY; MACROMOLECULE; PRIORITY JOURNAL; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; BENZ(A)ANTHRACENES; COUMARINS; CRYSTALLOGRAPHY; HYDROGEN BONDING; MOLECULAR STRUCTURE;

EID: 0029806419     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.10.2245     Document Type: Article

References (23)

1. DiGiovanni, J. (1990) Inhibition of chemical carcinogenesis. In Cooper, C.S. and Grover, P.L. (eds), Handbook of Experimental Pharmacology. Springer-Verlag, New York, vol. 94/II, pp. 159-223.
2. Dean, F.M. (1963) Naturally Occurring Oxygen Ring Compounds. Butterworth, London, UK. pp. 176-219.
3. Robinson, T. (1963) The Organic Constituents of Higher Plants. Burgess, Minneapolis, MN, pp. 45-69.
4. Feuer, G. and Kellen, J.A. (1974) Inhibition and enhancement of mammary tumorigenesis by 7,12-dimethylbenz[a]anthracene in the female Sprague-Dawley rat. Int. J. Clin. Pharmacol., 9, 62-69.
5. Feuer, G., Kellen, J.A. and Kovacs, K. (1976) Suppression of 7,12-dimethylbenz[a]anthracene-induced breast carcinoma by coumarin in the rat. Oncology, 33, 35-39.
6. Wattenberg, L.W., Lam, L.K.T. and Fladmoe, A.V. (1979) Inhibition of chemical carcinogen-induced neoplasia by coumarins and α-angelicalactone. Cancer Res., 39, 1651-1654.
7. Harvey, R.G., Cortez, C., Ananthanarayan, T.P. and Schmolka, S. (1988) A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties. J. Org. Chem., 53, 3936-3943.
8. Harvey, R.G., Hahn, J.-T., Bukowska, M. and Jackson, H. (1990) A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones. J. Org. Chem., 55, 6161-6166.
9. Nair, R.V., Fisher, E.P., Safe, S.H., Cortez, C., Harvey, R.G. and DiGiovanni, J. (1991) Novel coumarins as potential anticarcinogenic agents. Carcinogenesis, 12, 65-69.
10. Pflugrath, J. and Messerschmitt, A. (1989) MADNES, Munich Area Detector (New EEC) System, version EEC 11/09/89, with enhancements by Enraf-Nonius Corporation, Delft, The Netherlands.
11. Karaulov, C. (1991) ABSURD - program to aid in processing data from MADNES, modified for space group determination.
12. Kabsch, W. (1988) Evaluation of single-crystal X-ray diffraction data from a position-sensitive detector. J. Appl. Crystallogr., 21, 916-924.
13. Carrell, H.L., Shieh, H.-S. and Takusagawa, F. (1981) Crystallographic Program Library, Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, PA.
14. Beevers, C.A. and Robertson, J.H. (1950) Interpretation of the Patterson synthesis. Acta Crystallogr, 3, 164.
15. Gantzel, P.K., Sparks, R.A., Long, R.E. and Trueblood, K.N. (1969) UCLALS4, program in Fortran IV.
16. Carrell, H.L. (1975) ICRFMLS, a modification of UCLALS4. The Institute for Cancer Research, The Fox Chase Cancer Center.
17. Ibers, J.A. and Hamilton, W.C. (Eds) (1974) International Tables for X-ray Crystallography Vol. IV. Kynoch Press, Birmingham, UK (present distributor Kluwer Academic Publishers, Dordrecht, The Netherlands).
18. Erlebacher, J. and Carrell, H.L. (1992) ICRVIEW. Institute for Cancer Research, The Fox Chase Cancer Center, Philadelphia, PA.
19. Prochaska, H.J., De Long, M.J. and Talalay, P. (1985) On the mechanism of induction of cancer protective enzymes: a unifying proposal. Proc. Natl Acad. Sci. USA, 82, 8232-8236.
20. Prochaska, H.J. and Talalay, P. (1988) Regulating mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Res., 48, 4776-4782.
21. Talalay, P., De Long, M.J. and Prochaska, H.J. (1988) Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl Acad. Sci. USA, 85, 8261-8265.
22. Shimoni, L., Carrell, H.L., Glusker, J.P. and Coombs, M.M. (1994) Intermolecular effects in crystals of 11-(trifluoromethyl)-15,16-dihydrocyclopenta[a]phenanthren-17-one. J. Am. Chem. Soc., 116, 8162-8168.
23. Allen, F.H., Bellard, S., Brice, M.D. et al. (1979) The Cambridge Crystallographic Data Centre: computer-based search, retrieval, analysis and display of information. Acta Crystallogr., B35, 2331-2339.