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

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