The reduction of 2-bromomethyl-3-methyl- and 2,3-bis-bromomethyl-1,4-naphthoquinones, potential bioreductive alkylating agents. Electrochemical and computational studies

Journal of Electroanalytical Chemistry

Volumn 560, Issue 1, 2003, Pages 79-86

  De Abreu, Fabiane C ^a,b   Lopes, Adriana C O ^a   Do Monte, Silmar A ^b   Soares, Nivaldo A ^a   Goulart, Marília O F ^a  

^a FEDERAL UNIVERSITY OF ALAGOAS   (Brazil)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

2,3 Bis methylbromo 1,4 naphthoquinone; 2 Methylbromo 3 methyl 1,4 naphthoquinone; Cyclic voltammetry; Leaving group effect; Redox potential; Reductive elimination

Indexed keywords

BROMINE; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTRODES; ELECTROLYSIS; REDOX REACTIONS; REDUCTION;

LEAVING GROUP EFFECT;

ORGANIC COMPOUNDS;

EID: 0242573430     PISSN: 15726657     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jelechem.2003.07.021     Document Type: Article

References (35)

1. Rajski S.R., Williams R.M. Chem. Rev. 98:1998;2723.
2. Lin A.J., Cosby L.A., Shansky C.W., Sartorelli A.C. J. Med. Chem. 15:1972;1247.
3. Lin A.J., Pardini R.S., Cosby L.A., Lillis B.J., Shansky C.W., Sartorelli A.C. J. Med. Chem. 16:1973;1268.
4. Lin A.J., Pardini R.S., Cosby L.A., Lillis B.J., Sartorelli A.C. J. Med. Chem. 17:1974;558.
5. Lin A.J., Lillis B.J., Sartorelli A.C. J. Med. Chem. 18:1975;917.
6. Lin A.J., Sartorelli A.C. Biochem. Pharmacol. 25:1976;206.
7. Prakash G., Hodnett E.M. J. Med. Chem. 21:1978;369.
8. Li C-Y., Jenq J. Electrochim. Acta. 36:1991;269.
9. Livertoux M-H., Lagrange P., Minn A. Brain Res. 725:1996;207.
10. Kovacic P., Ames J.R., Grogan J.W., Hazra B., Ryan M.D. Dryhurst G., Niki K. Redox Chemistry and Interfacial Behaviour of Biological Molecules. 1989;295-307 Plenum Press, New York.
11. Wilson I., Wardman P., Lin T.-S., Sartorelli A.C. J. Med. Chem. 29:1986;1381.
12. Giulivi C., Cadenas E. Biochem. J. 301:1994;21.
13. Goulart M.O.F., Zani C.L., Tonholo J., Freitas L.R., de Abreu F.C., Raslan D.S., Starling S., de Oliveira A.B., Chiari E. Bioorg. Med. Chem. Lett. 7:1997;2043.
14. de Paula F.S., Cioletti A.G., da Silva Fo J.F., Santana A.E.G., dos Santos A.F., Goulart M.O.F., Vallaro M., Fruttero R. J. Electroanal. Chem. 544:2003;25.
15. Savéant J.-M. Adv. Phys. Org. Chem. 35:2000;117.
16. Maran F., Wayner D.D.M., Worketin M.S. Adv. Phys. Org. Chem. 36:2001;85.
17. Antonello S., Crisma M., Formaggio F., Moretto A., Taddel F., Toniolo C., Maran F. J. Am. Chem. Soc. 124:2002;11503.
18. Lin A.J., Antonini I., Cosby L.A., Sartorelli A.C. J. Med. Chem. 27:1984;813.
19. Ferreira V.F., Pinto A.V., Pinto M.C.F.R., Santos S.C. J. Braz. Chem. Soc. 7:1996;169.
20. Goulart M.O.F., de Abreu F.C., Lopez A.C.O., Pereira M.A., de Simone C.A. Tetrahedron Lett. 2002;8153.
21. Hawley M.D. Bard A.J., Lund H. Encyclopedia of Electrochemistry of the Elements. vol. XIV:1980;Marcel Dekker, New York.
22. Peters D.G. Lund H., Baizer M.M. Organic Electrochemistry. third ed. 1991;362-393 Marcel Dekker, New York.
23. Casanova J., Reddy V.P. Patai S., Rappoport Z. The Chemistry of Halides, Pseudo-halides and Azides. 1995;1003-1067 Wiley, New York.
24. Simonet J., Martinet P., Doupeux H., Bretelle D. Bull. Soc. Chim. France. 1970;808.
25. Doupeux H., Simonet J. Bull. Soc. Chim. France. 1972;1219.
26. Laatsch H. Liebigs Ann. Chem. 1982;1808.
27. Lin A.J., Sartorelli A.C. J. Org. Chem. 38:1973;813.
28. Andrieux C.P., Savéant J.-M., Tallec A., Tardivel R., Tardy C. J. Am. Chem. Soc. 1997;2420.
29. Mikesell P., Schwaebe M., DiMare M., Little R.D. Acta Chem. Scand. 53:1999;792.
30. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A. Jr., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., Pople J.A. Gaussian 98, Revision A.7. 1998;Gaussian, Inc, Pittsburgh PA.
31. Wheeler R.A., Grafton A.K. J. Phys. Chem. A. 101:1997;7154.
32. David R. Lide (Ed.), CRC Handbook of Chemistry and Physics, 76th ed., (1995) Section 9-15.
33. Antonello S., Maran F. J. Am. Chem. Soc. 121:1999;9668.
34. Van de Water R.W., Petrus T.R.R. Tetrahedron. 58:2002;5367.
35. Rosenau T., Potthast A., Eleder T., Kosma P. Org. Lett. 4:2002;4285.