Cover

Title

Copyright

Contents

Authors' preface

Abbreviations employed in this book

Part 1 CHEMISTRY

Nomenclature and purification of BAs

1 Synthetic routes from benzenes and naphthalenes

1.1 The ketoacid route

1.2 Organometallic intermediates

1.3 The Elbs reaction

1.4 BAQs and the Hayashi rearrangement

1.5 Chemical reactivity of BA

2 Synthetic routes from anthracenes (A-ring formation)

2.1 Friedel-Crafts reactions

2.2 Rearrangement of spiro compounds

2.3 Reformatsky reactions

2.4 Robinson-Mannich synthesis and Michael reactions

2.5 Dienone-phenol rearrangement

2.6 Dieckmann cyclization

3 Synthetic routes from phenanthrenes (D-ring formation)

3.1 Friedel-Crafts reactions

3.2 1,4-Phenanthraquinone reactions

4 Synthetic Diels-Alder routes to rings B and C

4.1 Additions to 1,4-naphthoquinones

4.2 Route from substituted furans

4.3 Photochemical cyclizations

5 Miscellaneous synthetic routes

5.1 Diels-Alder reactions and Stobbe condensations

5.2 Friedel-Crafts alkylations

5.3 Grignard, Michael, Wittig and Vilsmeier reactions

5.4 Wagner-Meerwein and anthrasteroid rearrangements

5.5 Reactions involving lithiated species

5.6 Decarboxylative alkylation

5.7 Condensation, cyclodehydration

5.8 Isotopically labelled BAs

6 Tables

7 References to Part 1

Part 2 BIOLOGY

Historical aspects

8 Metabolism

8.1 Introduction

8.2 Metabolism of benz[a]anthracene

8.3 Metabolism of monosubstituted benz[a]anthracenes

8.3.1 1-Methylbenz[a]anthracene

8.3.2 4-Methylbenz[a]anthracene

8.3.3 6-Fluorobenz[a]anthracene

8.3.4 6-Methylbenz[a]anthracene

8.3.5 7-Methylbenz[a]anthracene

8.3.6 Other 7-substituted benz[a]anthracene derivatives

8.3.7 8-Methylbenz[a]anthracene

8.3.8 11-Methylbe nz[a]anthracene

8.3.9 12-Methylbenz[a]anthracene

8.4 Metabolism of disubstituted benz[a]anthracenes

8.4.1 5- and 5-Fluoro-7-methylbenz[a]anthracene

8.4.2 6-Fluoro-12-methylbenz[a] anthracene

8.4.3 7,12-Dimethylbenz[a]anthracene

8.5 Metabolism of trisubstituted benz[a]anthracenes

8.5.1 Fluorine-substituted 7,12-dimethylbenz[a]anthracenes

9 DNA, RNA and protein interactions

9.1 Introduction

9.2 Binding of benz[a]anthracene to DNA and RNA

9.3 Binding of monosubstituted benz[a]anthracenes to DNA and RNA

9.3.1 7-Methylbenz[a]anthracene

9.3.2 7-Bromomethylbenz[a]anthracene

9.3.3 7-Hydroxymethylbenz[a]anthracene

9.3.4 12-Methylbenz[a]anthracene

9.4 Binding of disubstituted benz[a]anthracenes to DNA and RNA

9.4.1 7J2'Dimethylbenz[a]anthracene

9.4.2 Reaction of 7,12-dimethylbenz[a]anthracene 5,6-epoxide withDNA

9.4.3 7-Hydroxymethyl-12-methylbenz[a]anthracene

9.4.4 7-Bromomethyl-12-methylbenz[a]anthracene

9.5 Binding of trisubstituted benz[a]anthracenes to DNA and RNA

9.5.1 Fluorine-substituted 7,12-dimethylbenz[a]anthracene

9.6 Interaction of benz[a]anthracene and substituted benzfa] anthracenes with proteins and peptides

10 Mutagenicity

10.1 Introduction

10.2 Mutagenicity of benz[a]anthracene

10.3 Mutagenicity of dihydrodiols and diol epoxides of benzfa] anthracene

10.4 Mutagenicity of monosubstituted benz[a]anthracenes

10.4.1 Alkyl derivatives

10.4.2 Halogen derivatives

10.4.3 Nitro derivatives

10.4.4 Oxy derivatives

10.5 Mutagenicity of disubstituted benz[a]anthracenes

10.5.1 Alkyl derivatives

10.6 Mutagenicity of trisubstituted benz[a]anthracenes

11 Carcinogenicity

11.1 Introduction

11.2 Carcinogenicity of benz[a]anthracene

11.3 Carcinogenicity of metabolites of benz[a] anthracene

11.4 Carcinogenicity of monosubstituted benz[a]anthracenes

11.4.1 Alky I derivatives

11.4.2 Halogen derivatives

11.4.3 Nitro derivatives

11.4.4 Amino derivatives

11.4.5 Hydroxyl derivatives

11.4.6 Oxo derivatives

11.4.7 Carboxy derivatives

11.4.8 Thiol derivatives

11.5 Carcinogenicity of disubstituted benz[a]anthracenes

11.5.1 Alkyl derivatives

11.6 Carcinogenicity of trisubstituted benz[a] anthracenes

11.6.1 Alky I derivatives

11.6.2 Halogen derivatives

11.6.3 Other trisubstituted derivatives

11.7 Carcinogenicity of tetrasubstituted benz[a] anthracene

12 References to Part 2

Index to Parts 1 and 2