Contents

Page The numbering of the acridine ring Front end paper Preface v

Notes on numbering the acridine ring XI

PART I: PREPARATIVE METHODS CHAPTER 1 lnterconversion of acridines, acridones, and acridans 3 2 Synthesis of acridones and 9-chloroacridines by ring-closure of diphenylamine-2-carboxylic acids 29 3 The preparation of diphenylamine-2-carboxylic acids (phenylan- thranilic acids) as starting material for the reactions of Chapter 2 56 4 Synthesis of acridines by ring-closure of diphenylamine-2-alde- hydes, and -2-ketones 78 5 Synthesis of acridines from diphenylamine and organic acids. --' diphenylamines 91 of acridines from m-phenylenediamine(s) and formic 103 from aromatic amines and aldehydes, or from 114 , acridines, and acridans 131 AA~...~ choose a suitable preparative method. Hints on the mani- pulation and purification of acridines 143

PART II: PHYSICAL PROPERTIES

10 Surface Activity and Association. Ionization. Dipole Moments 155 II Spectra. Fluorescence and phosphorescence 176

PART Ill: CHEMICAL PROPERTIES

12 Chemical properties of acridines (excluding aminoacridines) 233 Alkyl-, aryl-, halogeno-, alkoxy-, hydroxy-, nitro-, and cyano- acridines 245 Acridine-aldehydes, -ketones, -carboxylic acids, -sulphonic acids, -arsonic acids, and -stibonic acids; also their derivatives 266 Nitrogen-oxides, thio-ethers, seleno-ethers 269 Benzacridines 274 13 Aminoacridines with no C-substituent 284 Amina<;:rine, Proflavine, Acridine Orange 1. x Contents

CHAPTER 14 Aminoacridines bearing C-substituents Ethacridine (' Rivanol'), , Entozon " Mepacrine (Quinacrine, , Atebrin '), Aminoacrichine, ' Azacrin " ' Acranil' Acridine Yellow , Benzoflavine, Chrysaniline, Flaveosin, Phos- phine, Rheonine 15 Quaternary acridines Acriflavine, Euflavine, ' Trypafiavin', ' Diamond Phosphine' and other quaternized dyes 16 Acridans, and other hydroacridines Tacrine (tetrahydro-aminacrine). Carbazons, Carbazims 17 Acridones, thio- and seleno-acridones, tetrahydroacridones 18 Binuclear acridines Biacridyls, biacridylidenes, biacridanyls, Luzigenin, Biacridonyls

PART IV: BIOLOGI,CAL PROPERTIES AND USES 19 The utilization of acridines in clinical medicine

General review. Antibacterials. Antimalarials 403

Anthelmintics. Anti-immune substances 430 Analeptics, and Morphine antagonists. .d.11 20 The connexion between antibacterial action and physicochemical properties in the acridine series 21 The connexion between antimalarial action and chemical structure in the acridine series. Trypanocidal action 22 Complexes of acridines with nucleic acid. Vital staining, antiviral action, mutogenesis, antimitotic activity 23 Vertebrate pharmacology and toxicology of acridines. Action on enzymes. Carcinogenicity and anticarcinogenicity

PART V: DYES AND REAGENTS , 24 The utilization of acridines as pigments and dyestuffs 25 Other applications of acridines. Analytical uses, Antioxidants and corrosion inhibitors, Biochemical Reagents, Chemiluminescence, Energy Cells, Industrial disinfection and preservation, Micro- scopical reagents, Photographic reagents

References Subject Index Index to preparations

Frontispiece. Reproduction of Graebe and Carols description of acridine in Annalen (facing title page)

Plate Atomic models of the cations of 9-aminoacridine (left- hand pair) and its 1-, 2-, 3-, 4-tetrahydro-analogue (right-hand pair) (facing p. 452)