The Sulfonamides and Allied CompoundsPDF电子书下载

Chapter Ⅰ．History of Bacterial Chemotherapy 1

(Ⅰ)DYES 1

(Ⅱ)SEARCH FOR AN AGENT ACTIVE in Vivo 1

(Ⅲ)PRONTOSIL 2

(Ⅳ)SULFANILAMIDE 3

(Ⅴ)SULFAPYRIDINE 4

(Ⅵ)MODERN SULFA DRUGS 4

(Ⅶ)THEORIES 5

(Ⅷ)FUTURE DEVELOPMENTS IN CHEMOTHERAPY 5

Chapter Ⅱ．Nomenclature，Classification and Synthesis of Sulfanilamide Derivatives 7

(Ⅰ)NOMENCLATURE 7

(A)SULFANILAMIDE DERIVATIVES 7

(B)SULFONES，SULFOXIDES，SULFIDES AND DISULFIDES 9

(Ⅱ)SYSTEM OF CLASSIFICATION 10

(A)GENERAL CONSIDERATIONS 10

(B)CLASSIFICATION OF SULFANILAMIDE DERIVATIVES 10

(C)CLASSIFICATION OF COMPOUNDS RELATED TO SULFANILAMIDE 11

(D)CLASSIFICATION OF SULFONES，SULFOXIDES，SULFIDES，DISULFIDES，ETC 11

(Ⅲ)SYNTHESIS OF SULFANILAMIDE DERIVATIVES AND SULFONES 11

(A)INTERMEDIATES 11

(B)MANUFACTURE OF SULFANILAMIDE 12

(C)MANUFACTURE OF SULFAPYRIDINE 13

(D)MANUFACTURE OF SULFATHIAZOLE AND DERIVATIVES 15

(E)MANUFACTURE OF SULFAGUANIDINE 16

(F)MANUFACTURE OF SULFADIAZINE 17

(G)MANUFACTURE OF SULFAMERAZINE(2-SULFANILAMIDO-4-METHYLPYRIMIDINE) 18

(H)MANUFACTURE OF＂SULFAMETHAZINE＂(2-SULFANILAMIDO-4，6-DIMETHYLPYRIMIDINE) 19

(I)MANUFACTURE OF BIS(4-AMINOPHENYL)SULFONE AND DERIVATIVES 19

Chapter Ⅲ．Structure and Activities of Simple Sulfanilamide Derivatives 21

(Ⅰ)SALTS OF SULFANILAMIDE(1-3：51) 21

(Ⅱ)NUCLEAR-SUBSTITUTED SULFANILAMIDES(4，5：52) 21

(Ⅲ)N1-SUBSTITUTED SULFANILAMIDES 21

(A)N1-Acyclicsulfanilamides 21

(B)N1-Isocyclicsulfanilamides 23

(C)N1-Heterocyclicsulfanilamides 25

(D)N1-Acylsulfanilamides 37

(E)N1-Inorganic Derivatives of Sulfanilamide 42

(Ⅳ)N4-SUBSTITUTED SULFANILAMIDES 43

(A)N4-Ayclicsulfanilamides(53：108) 43

(B)N4-Isocyclicsulfanilamides(54：109) 45

(C)N4-Heterocyclicsulfanilamides(55-58：110-117) 45

(D)N4-Anils of Sulfanilamide 45

(E)N4-Sugar Derivatives of Sulfanilamide 46

(F)N4-Acylsulfanilamides(65-68：123-129) 47

(G)N4-Inorganic Derivatives of Sulfanilamide 48

Chapter Ⅳ．Structure and Activities of Complex Sulfanilamide Derivatives 149

(Ⅰ)NUCLEAR-N1-SUBSTITUTED SULFANILAMIDES 149

(Ⅱ)NUCLEAR-N4-SUBSTITUTED SULFANILAMIDES 149

(Ⅲ)N1，N4-SUBSTITUTED SULFANILAMIDES 149

(A)N4-Acyclic-N1-substituted Sulfanilamides(92：162) 149

(B)N4-Isocyclic-N1-substituted Sulfanilamides(93：165) 149

(C)N4-Heterocyclic-N1-substituted Sulfanilamides(94，95：166，167) 150

(D)N4-Anils of N1-substituted Sulfanilamides(96：168) 150

(E)N4-Sugar Derivatives of N1-substituted Sulfanilamides(97，98：170，171) 150

(F)N4-Acyl-N1-substituted Sulfanilamides 150

(G)N4-Inorganic Derivatives of N1-Substituted Sulfanilamides 154

(Ⅳ)NUCLEAR-N1，N4-SUBSTITUTED SULFANILAMIDES(145：246) 155

(Ⅴ)UNCLASSIFIED DERIVATIVES OF SULFANILAMIDE(146：248) 155

Chapter Ⅴ．Structure and Activities of Compounds Related to Sulfanilamide 250

(Ⅰ)4-NITROBENZENESULFONAMIDES 250

(Ⅱ)DERIVATIVES OF ORTHANILAMIDE AND METANILAMIDE 251

(Ⅲ)ACYCLIC COMPOUNDS(170-173：280-281) 252

(Ⅳ)ISOCYCLIC COMPOUNDS 252

(A)Isocyclicsulfonamides 252

(B)Derivatives of 4-Aminobenzoic Acid 254

(C)Derivatives of 4-Nitrobenzoic Acid 256

(D)Derivatives of Sulfanilic Acid(190：304) 257

(E)Ketones 257

(F)Quinones(193：307) 258

(G)Isocyclicsulfenamides 258

(H)Derivatives of Isocyclicsulfinic Acids 258

(I)Isocyclic Selenium Compounds(198：311) 258

(J)Miscellaneous Isocyclicamines(199：311) 259

(K)Miscellaneous Azo Compounds(200：317) 259

(L)Miscellaneous Isocyclic Compounds(201：318) 259

(Ⅴ)HETEROCYCLIC COMPOUNDS 259

(A)Heterocyclicsulfonamides 259

(B)Miscellaneous Heterocyclic Compounds(217：335) 261

Chapter Ⅵ．Structure and Activities of Sulfones 340

(Ⅰ)ACYCLIC ISOCYCLIC SULFONES 340

(A)4-Aminophenyl Acyclic Sulfones 340

(B)Miscellaneous Acyclic Isocyclic Sulfones(222：350) 340

(Ⅱ)BIS(ISOCYCLIC)SULFONES 341

(A)Symmetrically Substituted Bis(4-aminophenyl)Sulfones 341

(B)Unsymmetrical Bis(4-aminophenyl)Sulfones with One 4-Aminophenyl Group Substituted 341

(C)Unsymmetrical Bis(4-aminophenyl)Sulfones with Both Nitrogens Substituted 344

(D)4-Aminophenyl Isocyclic Sulfones 345

(E)Miscellaneous Symmetrical Bis(isocyclic)Sulfones(248：369) 345

(F)Miscellaneous Unsymmetrical Bis(isocyclic)Sulfones(249：369) 346

(Ⅲ)ISOCYCLIC HETEROCYCLIC SULFONES 346

(A)Sulfanilyl Heterocycles 346

(B)Miscellaneous Isocyclic Heterocyclic Sulfones(252：374) 347

(Ⅳ)BIS(HETEROCYCLIC)SULFONES 347

(Ⅴ)HETEROCYCLIC SULFONES WITH THE S-ATOM A MEMBER OF THE HETEROCYCLIC SYSTEM(255：376) 347

Chapter Ⅶ．Structure and Activities of Compounds Related to the Sulfones 377

(Ⅰ)SULFIDES 377

(Ⅱ)SULFOXIDES 377

(Ⅲ)DISULFIDES 377

(Ⅳ)MISCELLANEOUS DISULFOXIDES(270：387) 378

(Ⅴ)MISCELLANEOUS DISULFONES(271：387) 378

(Ⅵ)COMPOUNDS RELATED TO BIS(4-AMINOPHENYL)SULFONE 378

(A)Selenium and Tellurium Compounds(272：387) 378

(B)Phosphorus Compounds(273：388) 379

(C)Arsenic Compounds(274：388) 379

Chapter Ⅷ．Experimental Evaluation of Chemotherapeutic Activity 389

(Ⅰ)ANTIBACTERIAL ACTIVITY TESTS 389

(A)In Vitro Tests 390

(B)In Vivo Tests 396

(C)Relation of in Vitro to in Vivo Activity 402

(Ⅱ)EXPERIMENTAL EVALUATION OF CHEMOTHERAPEUTIC ACTIVITY PREPARATORY TO CLINICAL TRIAL 402

(Ⅲ)TABULATED SUMMARY：EXPERIMENTAL EVALUATION OF CHEMOTHERAPEUTIC ACTIVITY 403

(A)Experimental Activities of Sulfa Drugs and Sulfones 403

(B)References to Experimental Studies with Sulfonamides(298：412-6) 404

(C)Illustrative Data 404

Chapter Ⅸ．Relationship of Structure to Chemotherapeutic Activity 422

(Ⅰ)SUMMARY OF RELATIONSHIPS OF STRUCTURE TO CHEMOTHERAPEUTIC ACTIVITY 422

(A)Sulfanilamide Derivatives 422

(B)Compounds Related to Sulfanilamide 425

(C)Sulfones 425

(D)Compounds Related to the Sulfones 426

(Ⅱ)DISCUSSION OF VARIOUS CORRELATIONS BETWEEN STRUCTURE AND ACTIVITY 426

(Ⅲ)GENERAL CONCLUSIONS 427

(A)Classification of Drugs Having Sulfanilamide-Type Activity 427

(B)Discussion of Exceptions to Generalizations 42

(C)Requirements for Sulfanilamide-Type Activity 438

(D)Development of New Drugs 430

Chapter Ⅹ．Pharmacology of Sulfonamide and Sulfone Drugs 434

(Ⅰ)GENERAL CONSIDERATIONS 434

(Ⅱ)METHOD OF ASSAY IN BODY FLUIDS 436

(Ⅲ)DEVELOPMENT OF A NEW CHEMOTHERAPEUTIC DRUG 438

(A)Development Preparatory to Clinical Trial 438

(B)Studies Preparatory to General Clinical Use 441

Chapter Ⅺ．Theories of the Mechanism of Action of Sulfonamide Drugs 466

(Ⅰ)FACTS FUNDAMENTAL TO A THEORY OF ACTION 466

(A)Summary of the More Important Experimental Findings 466

(B)Sulfonamide Antagonists 467

(C)Sulfonamide Potentiators or Synergists 473

(D)Action of Sulfonamides on Bacterial Toxins 473

(E)Specificity of Action of Sulfanilamide Derivatives 473

(F)Drug Resistance 476

(G)Bacterial Population vs Concentration of Sulfa Drug Required for Bacteriostasis 479

(H)Effects of Sulfonamide Drugs on Enzymes 480

(Ⅱ)ESSENTIAL METABOLITE THEORIES 482

(A)Theory of Woods and Fildes 482

(B)Applications and Extensions of the Woods-Fildes Theory 484

(C)Theory of Kohn and Harris 493

(D)Theories Involving Ionization of Sulfonamides 494

(Ⅲ)MISCELLANEOUS THEORIES 506

(A)Peroxide-Anticatalase Theory 506

(B)Theory of Sevag，et al 507

(C)Theory of Synergism and Antagonism 508

(D)Postulation of Lee and Foley 509

(E)Postulation of Jensen and Schmith 509

(F)Adsorption Theories 509

(G)Postulations of Henry 510

(Ⅳ)CRITICAL EVALUATION OF VARIOUS THEORIES 510

Chapter Ⅻ．Clinical Evaluation of Sulfonamide Drugs 517

(Ⅰ)GENERAL CONSIDERATIONS 517

(A)Precepts of Chemotherapy 517

(Ⅱ)GENERAL INFECTIONS OF THE BODY ENDANGERING LIFE 518

(A)Streptococcal Infections 518

(B)Staphylococcal Infections 519

(C)Pneumonia 519

(D)Meningitis 521

(E)Tuberculosis 523

(F)Bubonic Plague 526

(Ⅲ)INTESTINAL DISEASES OF BACILLARY ORIGIN 526

(A)Classification of Organisms 526

(B)Bacillary Dysentery 526

(C)Ulcerative Colitis 531

(D)Typhoid 531

(E)Paratyphoid 531

(F)Asiatic Cholera 532

(Ⅳ)USE OF SULFONAMIDE DRUGS IN OTORHINOLARYNGOLOGY 532

(A)General Remarks 532

(B)Systemic Use of the Drugs in Nose and Throat Infections 533

(C)Local Use of the Sulfonamides in the Upper Respiratory Tract 535

(D)Otitis Media and Mastoiditis 536

(E)Use of Sulfa Drugs in Ophthalmology 537

(Ⅴ)SULFA DRUGS IN GENITO-URINARY INFECTIONS 538

(A)Venereal Diseases 538

(B)Prophylactic Use of Sulfa Drugs against Gonorrhea and Chancroid 540

(C)Miscellaneous Urinary Infections 541

(Ⅵ)PROPHYLACTIC USE OF SULFONAMIDES 542

(A)Meningitis 542

(B)Respiratory Infections 543

(C)Rheumatic Fever 543

(D)Bacillary Dysentery 544

(E)Scarlet Fever 544

(F)Drug Resistant Organisms in Prophylaxis 545

(G)Drug Toxicity in Prophylaxis 545

(Ⅶ)MINOR OR UNCERTAIN APPLICATIONS OF THE SULFA DRUGS 546

(A)Virus Diseases 546

(B)Protozoal Diseases 548

(C)Fungus Diseases 550

(D)Rickettsial Diseases 551

(E)Local Use in Dermatology 552

(F)Miscellaneous Uses 553

(Ⅷ)WOUND AND SURGICAL USES OF THE SULFA DRUGS 554

(A)Wounds 554

(B)Burns 558

(C)Abdominal Surgery 559

(Ⅸ)SULFA DRUGS IN VETERINARY MEDICINE 560

(Ⅹ)CLINICAL TOXICITIES 563

(A)General Remarks 563

(B)General Effects on the Whole Body 563

(C)Toxic Reactions to the Blood 563

(D)Toxic Effects on the Nervous System 565

(E)Toxic Action on the Kidney 566

(F)Toxic Action on the Liver 569

(G)Toxic Action on the Heart 569

(H)Skin Reactions 569

(I)Toxic Reactions to the Eyes 574

(J)Detoxification 574

(K)Clinical Incidence of Toxic Reactions to the Sulfonamide Drugs(323：577) 575

LIST OF JOURNALS SEARCHED 578

REFERENCES 579

APPENDIXES 631

A．Key to Activities and Organisms or Diseases 633

B．Trade Names for Sulfanilamide 636

C．Trade Names for Sulfanilamide Derivatives and Related Compounds 637

INDEX 649