Steric effects on the direct mutagenicity of N-acyloxy-N-alkoxyamides—Probes for drug–DNA interactions

Glover, 2008, N-Acyloxy-N-alkoxyamides—structure, properties, reactivity and biological activity, 35 Glover, 2009, N-Heteroatom-substituted hydroxamic esters, 839 Glover, 1998, Anomeric amides—structure, properties and reactivity, Tetrahedron, 54, 7229, 10.1016/S0040-4020(98)00197-5 Campbell, 1990, Solvolysis and mutagenesis of N-acetoxy-N-alkoxybenzamides—evidence for nitrenium ion formation, Tetrahedron Lett., 31, 5377, 10.1016/S0040-4039(00)98076-6 Campbell, 1991, Evidence for the formation of nitrenium ions in the acid-catalysed solvolysis of mutagenic N-acetoxy-N-alkoxybenzamides, J. Chem. Soc., Perkin Trans., 2, 2067, 10.1039/p29910002067 Campbell, 1992, Bimolecular reactions of mutagenic N-acetoxy-N-alkoxybenzamides and N-methylaniline, J. Chem. Soc., Perkin Trans., 2, 1661, 10.1039/p29920001661 Bonin, 1994, Reactive intermediates from the solvolysis of mutagenic O-alkyl N-acetoxybenzohydroxamates, J. Chem. Soc., Perkin Trans., 2, 1173, 10.1039/p29940001173 Bonin, 1998, A comparison of the reactivity and mutagenicity of N-benzoyloxy-N-benzyloxybenzamides, J. Org. Chem., 63, 9684, 10.1021/jo980863z Campbell, 1999, (Synopsis)Bimolecular reactions of mutagenic N-(acyloxy)-N-alkoxybenzamides with aromatic amines, J. Chem. Res. (S), 8, 474, 10.1039/a903555i Campbell, 1999, (Microfiche) Bimolecular reactions of mutagenic N-(acyloxy)-N-alkoxybenzamides with aromatic amines, J. Chem. Res. (M), 8, 2075 Glover, 2002, 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, 1728, 10.1039/B111250N Banks, 2003 Cavanagh, 2009, SN2 substitution reactions at the amide nitrogen in the anomeric mutagens, N-acyloxy-N-alkoxyamides, Aust. J. Chem., 62, 700, 10.1071/CH09166 S.A. Glover, SN2 reactions at amide nitrogen—theoretical models for reactions of mutagenic N-acyloxy-N-alkoxyamides with bionucleophiles, Arkivoc Part xii, Issue in Honour of O.S.Tee, ms. OT-308C (2001) 143–160. Gerdes, 1989, N-Acetoxy-N-alkoxyamides—a new class of nitrenium ion precursors which are mutagenic, Tetrahedron Lett., 30, 2649, 10.1016/S0040-4039(00)99089-0 Bonin, 2001, Mutagenicity of electrophilic N-acyloxy-N-alkoxyamides, Mutat. Res., 494, 115, 10.1016/S1383-5718(01)00189-9 Banks, 2003, Mutagenicity and DNA damage studies of N-acyloxy-N-alkoxyamides—the role of electrophilic nitrogen, Org. Biomol. Chem., 1, 2238, 10.1039/b301618h Andrews, 2004, Mutagenic N-acyloxy-N-alkoxyamides—probes for drug–DNA interactions, Aust. J. Chem., 57, 377, 10.1071/CH03276 Andrews, 2006, The role of steric effects in the direct mutagenesis of N-acyloxy-N-alkoxyamides, Mutat. Res., 605, 51, 10.1016/j.mrgentox.2006.02.003 Ghose, 1988, Atomic physicochemical parameters for three dimensional structure directed quantitative structure–activity relationships III: modelling hydrophobic interactions, J. Comp. Chem., 9, 80, 10.1002/jcc.540090111 Glover, 1984, N-Alkoxy-N-acylnitrenium ions as possible intermediates in intramolecular aromatic substitution: novel formation of N-acyl-3,4-dihydro-1H-2,1-benzoxazines and N-acyl-4,5-dihydro-1H-2,1-benzoxazepine, J. Chem. Soc., Perkin Trans., 1, 2255, 10.1039/p19840002255 Glover, 1987, N-Alkoxy-N-acylnitrenium ions in intramolecular aromatic addition reactions, Tetrahedron, 43, 2577, 10.1016/S0040-4020(01)81665-3 Glover, 1989, MNDO properties of heteroatom and phenyl substituted nitrenium ions, Tetrahedron, 45, 1763, 10.1016/S0040-4020(01)80041-7 Kikugawa, 1984, Electrophilic aromatic substitution with a nitrenium ion generated from N-chloro-N-methoxyamides. Application to the synthesis of 1-methoxy-2-oxindoles, J. Am. Chem. Soc., 106, 5728, 10.1021/ja00331a053 Kikugawa, 1987, Intramolecular cyclization with nitrenium ions generated from N-chloro-N-methoxyamides in neutral conditions, Chem. Lett., 1771, 10.1246/cl.1987.1771 Kikugawa, 1994, Cyclization with nitrenium ions generated from N-methoxy- or N-allyloxy-N-chloroamides with anhydrous zinc acetate. Synthesis of N-methoxynitrogen heterocyclic compounds, Heterocycles, 37, 293, 10.3987/COM-93-S1 1988 Thorpe, 1973, Stereochemical and steric effects in nucleophilic substitution of α-halo ketones, Can. J. Chem., 51, 927, 10.1139/v73-137 Maron, 1983, Revised methods for Salmonella mutagenicity tests, Mutat. Res., 113, 173, 10.1016/0165-1161(83)90010-9 Mortelmans, 2000, The Ames Salmonella/microsome mutagenicity assay, Mutat. Res., 455, 29, 10.1016/S0027-5107(00)00064-6 2008 Hansch, 1995 ACD/LogP Web Service 5.0, Advanced Chemistry Development Inc. Ferguson, 1979, Potential antitumour agents. 30. Mutagenic activity of some 9-anilinoacridines: relationships between structure, mutagenic potential and antileukemic activity., J. Med. Chem., 22, 251, 10.1021/jm00189a006 Ferguson, 1980, Potential antitumour agents. 33. Quantitative structure–activity relationships for mutagenic activity and antitumour activity of substituted 4′-(9-acridinylamino)methanesulfonanilide derivatives, J. Med. Chem., 23, 269, 10.1021/jm00177a011 Hansch, 1995 Leo, 1981, Comparison of mutagenic and carcinogenic activities of aniline mustards, J. Med. Chem., 24, 859, 10.1021/jm00139a018 Debnath, 1994, The importance of the hydrophobic interaction in the mutagenicity of organic compounds, Mutat. Res., 305, 63, 10.1016/0027-5107(94)90126-0 Tuppurainen, 1999, Frontier orbital energies, hydrophobicity and steric factors as physical QSAR descriptors of molecular mutagenicity. A review with a case study: MX compounds, Chemosphere, 38, 3015, 10.1016/S0045-6535(98)00503-7 Debnath, 1993, The importance of hydrophobicity in the mutagenicity of methanesulfonic acid esters with Salmonella typhimurium TA100, Chem. Res. Toxcol., 6, 310, 10.1021/tx00033a009