A role for dipole moment in the activity of cyclolignans

Journal of Molecular Structure: THEOCHEM

Volumn 504, Issue 1-3, 2000, Pages 51-57

  Lopez Perez J L ^a   Del Olmo, E ^a   De Pascual Teresa, B ^b   Merino, M ^a   Barajas, M ^a   San Feliciano, A ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b Urbanización Monteprincipe   (Spain)

Author keywords

Deoxypodophyllotoxin; Dipole moment; Lignans; Podophyllotoxin; Podophyllotoxone

Indexed keywords

CYCLOLIGNAN; ETOPOSIDE; LIGNAN DERIVATIVE; PODOPHYLLOTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIPOLE; MOLECULAR MODEL; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0343526798     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(00)00354-7     Document Type: Article

References (27)

1. Cortese F., Bhattacharyya B., Wolff P. J. Biol. Chem. 252:1977;1134.
2. Saulnier M.G., LeBoulluec K.L., McGee D.P.P., Long B.H., Crosswell A.R., Vyas D.M. Bioorg. Med. Chem. Lett. 3:1993;1619.
3. Issel B.F., Louie A.R., Doyle A.C. Etoposide: [VP-16] Current Status and New Development. 1984;Academic Press, New York.
4. Ayrens D.C., Loike J.D. Lignans. Chemical, Biological and Clinical Properties. 1990;Cambridge University Press, Cambridge.
5. Sackett D.L. Pharm. Ther. 59:1993;163.
6. Jardin I. Podophyllotoxin. Cassady J.M., Douros J.D. Anticancer Agents Based on Natural Products Models. 1980;319-351 Academic Press, New York.
7. Loike J.D., Brewer C.F., Sternlicht H., Gensler W.J., Horwitz S.B. Cancer Res. 38:1978;2688.
8. Alton P.A., Harris A.L. Br. J. Haematol. 85:1993;241.
9. Osheroff N., Zechiedrich E.L., Gale K.C. BioEssays. 13:1991;269.
10. Liu L.F. Annu. Rev. Biochem. 58:1989;351.
11. Cho S.J., Tropsha A., Suffness M., Cheng Y.-C., Lee K.-H. J. Med. Chem. 39:1996;1383.
12. Eich E., Schulz J., Kalonga M., Merz H., Schöder H.C., Müller W.E.G. Planta Med. 57. 2:1991;A7. (Suppl. issue).
13. Gordaliza M., Miguel del Corral J.M., Castro M.A., López-Vazquez M.L., San Feliciano A., García-Grávalos M.D., Carpy A. Bioorg. Med. Chem. Lett. 3:1995;1203.
14. Wang J.-Z., Tian X., Tsumura H., Shimura K., Ito H. Anti-Cancer Drug Des. 8:1993;193.
15. Weintraub L., Terrell R. J. Org. Chem. 30:1965;2470.
16. Dickens J. Brit. Med. Bull. 20:1964;96.
17. Roberts J.J., Warwick G.P. Biochem. Pharmacol. 12:1963;1441.
18. Brookes P., Lawley P.D. Brit. Med. Bull. 20:1964;91.
19. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440.
20. Allinger N.L. J. Am. Chem. Soc. 99:1977;8127.
21. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, H.B. Foresman, G. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, J.A. Pople, GAUSSIAN 92, Revision D.2, Gaussian, Inc., Pittsburgh, PA, 1992.
22. SPARTAN version 4.0.1, Wavefunction, Inc., Irvine, CA.
23. Yamamoto D., Ohishi H., Kozawa M., Inamori Y., Ishida T., Inoue M. Chem. Pharm. Bull. 36:1988;3239.
24. Yamaguchi H., Arimoto M., Tanoguchi M., Ishida T., Inoue M. Chem. Pharm. Bull. 30:1982;3212.
25. Yamaguchi H., Nakajima S., Arimoto M., Tanoguchi M., Ishida T., Inoue M. Chem. Pharm. Bull. 32:1984;1754.
26. Singh U.C., Kollman P.A. J. Comput. Chem. 5:1984;129.
27. López-Pérez J.L., Olmo del E., Pascual-Teresa de B., Merino M., San Feliciano A. Tetrahedron. 52:1996;4903.