The Chemistry and Biology of Benz a anthracenes (Cambridge Monographs on Cancer Research)

First published in 1988, this volume surveys the chemical synthesis and biological activity of the benz[a]anthracenes. These compounds occur in smoke and mineral oils and a few have been shown to be potent carcinogens. This volume was the first to review, systematically and in depth, the organic synthesis of these compounds as well as their metablolism, interactions with nucleic acids and protein, mutagenicity and carcinogenicity. Such studies have important implications in determining mechanism and specificity of chemically induced carcinogenesis. Cover......Page 1 Frontmatter......Page 2 Contents......Page 6 Authors' preface......Page 10 Abbreviations employed in this book......Page 12 Nomenclature and purification of BAs......Page 16 1.1 The ketoacid route......Page 18 1.2 Organometallic intermediates......Page 24 1.3 The Elbs reaction......Page 28 1.4 BAQs and the Hayashi rearrangement......Page 29 1.5 Chemical reactivity of BA......Page 33 2.1 Friedel--Crafts reactions......Page 36 2.3 Reformatsky reactions......Page 37 2.4 Robinson--Mannich synthesis and Michael reactions......Page 38 2.5 Dienone--phenol rearrangement......Page 39 2.6 Dieckmann cyclization......Page 40 3.1 Friedel--Crafts reactions......Page 42 3.2 1,4-Phenanthraquinone reactions......Page 45 4.1 Additions to 1,4-naphthoquinones......Page 46 4.2 Route from substituted furans......Page 48 4.3 Photochemical cyclizations......Page 49 5.1 Diels--Alder reactions and Stobbe condensations......Page 52 5.2 Friedel--Crafts alkylations......Page 54 5.3 Grignard, Michael, Wittig and Vilsmeier reactions......Page 56 5.4 Wagner--Meerwein and anthrasteroid rearrangements......Page 58 5.5 Reactions involving lithiated species......Page 59 5.6 Decarboxylative alkylation......Page 60 5.7 Condensation, cyclodehydration......Page 61 5.8 Isotopically labelled BAs......Page 62 6 - Tables......Page 64 7 - References to Part 1......Page 78 Historical aspects......Page 98 8.1 Introduction......Page 102 8.2 Metabolism of benz[a]anthracene......Page 105 8.3 Metabolism of monosubstituted benz[a]anthracenes......Page 111 8.4 Metabolism of disubstituted benz[a]anthracenes......Page 116 8.5 Metabolism of trisubstituted benz[a]anthracenes......Page 127 9.1 Introduction......Page 128 9.2 Binding of benz[a]anthracene to DNA and RNA......Page 129 9.3 Binding of monosubstituted benz[a]anthracenes to DNA and RNA......Page 133 9.4 Binding of disubstituted benz[a]anthracenes to DNA and RNA......Page 137 9.6 Interaction of benz[a]anthracene and substituted benz[a]anthracenes with proteins and peptides......Page 155 10.2 Mutagenicity of benz[a]anthracene......Page 159 10.3 Mutagenicity of dihydrodiols and diol epoxides of benz[a]anthracene......Page 160 10.4 Mutagenicity of monosubstituted benz[a]anthracenes......Page 163 10.5 Mutagenicity of disubstituted benz[a]anthracenes......Page 167 10.6 Mutagenicity of trisubstituted benz[a]anthracenes......Page 172 11.2 Carcinogenicity of benz[a]anthracene......Page 175 11.3 Carcinogenicity of metabolites of benz[a]anthracene......Page 176 11.4 Carcinogenicity of monosubstituted benz[a]anthracenes......Page 179 11.5 Carcinogenicity of disubstituted benz[a]anthracenes......Page 184 11.6 Carcinogenicity of trisubstituted benz[a]anthracenes......Page 197 11.7 Carcinogenicity of tetrasubstituted benz[a]anthracene......Page 200 12 - References to Part 2......Page 201 Index to Parts 1 and 2......Page 225 M.s. Newman, B. Tierney, S. Veeraraghavan. Includes Bibliographies And Index.