The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 605, Issue 1-2, 2006, Pages 51-62

  Andrews, Luke E ^a   Bonin, Antonio M ^b   Fransson, Linda E ^a   Gillson, Ashley Mae E ^a   Glover, Stephen A ^a  

^a UNIVERSITY OF NEW ENGLAND   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Ames Test; Amides; Direct acting; Electrophiles; Mutagenicity; QSAR; Steric effects

Indexed keywords

AMIDE; AMIDE CARBONYL; BENZAMIDE DERIVATIVE; CARBONYL DERIVATIVE; N ACYLOXY N ALKOXYAMIDE DERIVATIVE; N BENZOYLOXY N BENZYLOXYBENZAMIDE DERIVATIVE; N BENZOYLOXY N BUTOXYLALKYLAMIDE DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG; BACTERIAL DNA; GUANINE; MUTAGENIC AGENT;

ARTICLE; CHEMICAL REACTION; HYDROPHOBICITY; MUTAGENICITY; PH; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SYNTHESIS; BINDING SITE; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; GENETICS; GROWTH, DEVELOPMENT AND AGING; MUTAGEN TESTING; SALMONELLA ENTERICA SUBSP. ENTERICA SEROVAR TYPHIMURIUM; STRUCTURE ACTIVITY RELATION;

SALMONELLA TYPHIMURIUM;

BENZAMIDES; BINDING SITES; DNA, BACTERIAL; GUANINE; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MUTAGENICITY TESTS; MUTAGENS; POLYUNSATURATED ALKAMIDES; SALMONELLA TYPHIMURIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646793349     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrgentox.2006.02.003     Document Type: Article

References (29)

1. Gerdes R.G., Glover S.A., Ten Have J.F., and Rowbottom C.A. N-acetoxy-N-alkoxyamides - a new class of nitrenium ion precursors which are mutagenic. Tetrahedron Lett. 30 (1989) 2649-2652
2. Campbell J.J., Glover S.A., and Rowbottom C.A. Solvolysis and mutagenesis of N-acetoxy-N-alkoxybenzamides - evidence for nitrenium ion formation. Tetrahedron Lett. 31 (1990) 5377-5380
3. Campbell J.J., Glover S.A., Hammond G.P., and Rowbottom C.A. Evidence for the formation of nitrenium ions in the acid-catalysed solvolysis of mutagenic N-acetoxy-N-alkoxybenzamides. J. Chem. Soc.: Perkin Trans. 2 (1991) 2067-2079
4. Bonin A.M., Glover S.A., and Hammond G.P. Reactive intermediates from the solvolysis of mutagenic O-alkyl N-acetoxybenzohydroxamates. J. Chem. Soc.: Perkin Trans. 2 (1994) 1173-1180
5. Bonin A.M., Glover S.A., and Hammond G.P. A comparison of the reactivity and mutagenicity of N-benzoyloxy-N-benzyloxybenzamides. J. Org. Chem. 63 (1998) 9684-9689
6. Banks T.M., Bonin A.M., Campbell J.J., Glover S.A., Hammond G.P., Prakash A.S., and Rowbottom C.A. Mutagenicity of electrophilic N-acyloxy-N-alkoxyamides. Mutat. Res. 494 1-2 (2001) 115-134
7. Banks T.M., Bonin A.M., Glover S.A., and Prakash A.S. Mutagenicity and DNA damage studies of N-acyloxy-N-alkoxyamides-the role of electrophilic nitrogen. Org. Biomol. Chem. 1 (2003) 2238-2246
8. Andrews L.E., Banks T.M., Bonin A.M., Clay S.F., Gillson A.-M.E., and Glover S.A. Mutagenic N-acyloxy-N-alkoxyamides-probes for drug-DNA interactions. Aust. J. Chem. 57 (2004) 377-381
9. Tuppurainen K. Frontier orbital energies, hydrophobicity and steric factors as physical QSAR descriptors of molecular mutagenicity. A review with a case study: MX compounds. Chemosphere 38 (1999) 3015-3030
10. Debnath A.K., Shusterman A.J., Lopez de Compadre R.L., and Hansch C. The importance of the hydrophobic interaction in the mutagenicity of organic compounds. Mutat. Res. 305 (1994) 63-72
11. Hansch C., and Leo A.J. Exploring QSAR, Fundamentals and Applications in Chemistry and Biology. Part I (1995), American Chemical Society, Washington, DC
12. Gillson A.-M.E., Glover S.A., Tucker D.J., and Turner P. Crystal structures and properties of mutagenic N-acyloxy-N-alkoxyamides-"most pyramidal" acyclic amides. Org. Biomol. Chem. (2003) 3430-3437
13. Cooley J.H., Mosher M.W., and Khan M.A. Preparation and reactions of N,N′-diacyl-N,N′-dialkoxyhydrazines. J. Am. Chem. Soc. 90 (1968) 1867-1871
14. A.H. Blatt (Ed.), John Wiley & Sons, New York, 1957, p. 67.
15. Mintz M.J., and Walling C. t-Butyl hypochlorite. Org. Synth. 49 (1963) 9
16. Maron D.M., and Ames B.N. Revised methods for Salmonella mutagenicity tests. Mutat. Res. 113 (1983) 173-215
17. A.K. Ghose, A. Pritchett, G.M. Crippen, Atomic physicochemical parameters for three dimensional structure directed quntitative structure-activity relationships. III. Modelling hydrophobic interactions, J. Comp. Chem. 9 (1988) 80-90; MacSpartan Pro, Wavefunction Inc., 18401 Van Karman Avenue, Suite 370, Irvine, CA 92612, USA.
18. Glover S.A. SN2 reactions at amide nitrogen - theoretical models for reactions of mutagenic N-acyloxy-N-alkoxyamides with bionucleophiles. Arkivok xii (2001) 143-160
19. Banks T.M. Reactivity, Mutagenicity and DNA Damage of N-Acyloxy-N-Alkoxyamides (2003), University of New England
20. Glover S.A., and Mo G. Hindered ester formation by SN2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides-novel application of HERON rearrangements. J. Chem. Soc.: Perkin Trans. 2 (2002) 1728-1739
21. Glover S.A., and Rauk A. A computational investigation of the structure of the novel anomeric amide N-azido-N-methoxyformamide and its concerted decomposition to methyl formate and nitrogen. J. Chem. Soc.: Perkin Trans. 2 (2002) 1740-1746
22. Glover S.A. Anomeric amides-structure, properties and reactivity. Tetrahedron 54 (1998) 7229-7272
23. In: De Kimpe N., and Verhé R. (Eds). The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines (1988), John Wiley and Sons, Chichester
24. Thorpe J.W., and Warkentin J. Stereochemical and steric effects in nucleophilic substitution of α-halo ketones. Can. J. Chem. 51 (1973) 927-935
25. Campbell J.J., and Glover S.A. Bimolecular reactions of mutagenic N-(Acyloxy)-N-alkoxybenzamides with aromatic amines. J. Chem. Res. (S) 8 (1999) 474-475
26. Klein M., Erdinger L., and Boche G. From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of nitroaromatics in Salmonella typhimurium. Part II. Substituents far away from the nitro group. Mutat. Res. 467 (2000) 69-82
27. Glende C., Klein M., Schmitt H., Erdinger L., and Boche G. Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. Part II. Alkylation far away from the amino function. Mutat. Res. 515 (2002) 15-38
28. Klein M., Voigtmann U., Haack T., Erdinger L., and Boche G. From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of 4-nitrobiphenyl in Salmonella typhimurium. Part I. Substituents ortho to the nitro group and in 2′-position. Mutat. Res. 467 (2000) 55-68
29. Glende C., Schmitt H., Erdinger L., Engelhardt G., and Boche G. Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. Part I. Alkylation ortho to the amino function. Mutat. Res. 498 (2001) 19-37