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Strategies for Organic Drug Synthesis and Design

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Strategies for Organic Drug Synthesis and Design STRATEGIES FOR ORGANIC DRUG SYNTHESIS AND DESIGN DANIEL LEDNICER Rockvilte, MD A Wifey-lnterscience Publication John Wiley & Sons, Inc. New York / Chichester / Weinheim / Brisbane / Singapore / Toronto CONTENTS PREFACE xiii 1 PROSTAGLANDINS, PROTEASE INHIBITORS, AND RETINOIDS 1 1. Prostaglandins / 1 2. Protease Inhibitors / 17 3. Retinoids / 24 2 DRUGS BASED ON A SUBSTITUTED BENZENE RING 30 1. AryJethanol amines / 30 2. Ary]oxypropanolamines / 37 A. p-Blockers / 37 B. Nontricyclic Antidepressants / 41 3. Arylsulfonic Acid Derivatives / 42 A. Antibacterial Sulfonamides / 42 B. Diuretic Agents / 44 C. Oral Hypoglycemic Sulfonylureas / 47 D. Thromboxane Receptor Antagonists / 49 4. Arylacetic and Arylpropionic Acids / 49 A. Arylacetic Acid "Fenacs" / 49 B. Arylpropionic Acid "Profens" / 53 Viii CONTENTS C. Arylacetamide Antiarrhythmic Compounds / 57 D. Miscellaneous Compounds / 59 3 INDENES, NAPHTHALENES, AND OTHER POLYCYCLIC AROMATIC COMPOUNDS 63 1. Indenes / 63 2. Naphthalenes / 66 A. Antifungal Compounds / 66 B. Another (3-Blocker / 69 C. Aminotetralin Antidepressants / 70 3. Tricyclic Compounds / 72 A. Dibenzocycloheptane and Dibenzocycloheptene Antidepressants / 72 B. Antidepressants Based on Dihydroanthracenes / 76 C. Anthraquinones: The "Antrone" Chemotherapy Agents / 79 4 STEROIDS PART I: ESTRANES, GONANES, AND ANDROSTANES 84 3. Introduction / 84 2. Steroid Starting Materials / 85 A. From Diosgenin / 86 B. From Soybean Sterols / 86 3. Estranes / 88 A. Synthesis of Estranes / 88 B. Drugs Based on Estranes / 90 4. Gonanes:The 19-Nor Steroids / 92 A. Progestational Compounds / 92 B. Progesterone Antagonists / 101 C. Androgenic Compounds / 104 5. Androstanes / 106 A. Starting Materials / 106 B. Androgenic Compounds / 107 C. Aldosterone Antagonists / 115 CONTENTS IX 5 STEROIDS PART 2: COMPOUNDS RELATED TO PROGESTERONE AND CORTISONE 121 1. Introduction / I2l 2. Progestins / 12I 3. Corticosteroids / 129 6 NONSTEROIDAL ESTROGENS AND THEIR ANTAGONISTS 146 1. Introduction / 146 2. Synthetic Estrogens / 146 3. Nonsteroid Estrogen Antagonists / 150 7 OPIOID ANALGESICS 161 1. Introduction / 161 2. Drugs Derived from Morphine / 162 3. Compounds Prepared from Thebaine / 164 4. Morphinans / 167 5. Benzomorphans / 170 6. Analgesics Based on Nonfused Piperidines / 175 A. 4-Arylpipridines: Meperidine and Its Analogues / 175 B. 4-Amidopiperidines: Compounds Related to Fentanyl / 178 8 DRUGS BASED ON FIVE-MEMBER ED HETEROCYCLES 185 1. Introduction / 185 2. Rings with One Heteroatom / 185 A. Furans / 185 B. Pyrrole and Its Derivatives / 190 3. Rings with Two Heteroatoms / 200 A. Oxazoles, tsoxazoles, and Their Derivatives / 200 B. Imidazoles / 207 C. Pyrrazolones and Pyrrazolodiones / 225 D. Thiazoles and Related Sulfur-Nitrogen-Containing Heterocycles / 227 4. Rings with Three or More Heteroatoms / 232 A. 1,2,4-Oxadiazoles / 232 B. Triazoles / 233 X CONTENTS C. Thiadiazoles / 236 D. Tetrazole / 238 9 DRUGS BASED ON SIX-MEMBERED HETEROCYCLES 242 1. Rings with One Heteroatom / 242 A. Pyridines / 242 B. 1,4-Dihydropyridines / 245 C. Piperidines / 250 D. Pyridones and Glutarimides / 254 2. Rings with Two Heteroatoms / 257 A. Pyridazines / 257 B. Pyrimidines / 260 C. Pyrimidine Nucleosides / 265 D. Pyrimidones / 268 E. Triketopyri mi dines: The Barbiturates / 272 F. Pyrazines and Piperazines / 272 3. Rings with Three Heteroatoms: The Triazines / 280 10 FIVE-MEMBERED HETEROCYCLES FUSED TO A BENZENE RING 286 1. Compounds with One Heteroatom / 286 A. Benzofurans / 286 B. Indoles / 289 C. Indolinesand Isoindolines / 296 2. Compounds with Two Heteroatoms / 299 A. Indazoles / 299 B. Benzimidazoles / 300 C. Benzothiazoles / 307 11 SIX-MEMBERED HETEROCYCLES FUSED TO A BENZENE RING 311 1. Compounds with One Heteroatom / 311 A. Coumarins / 311 B. Chromones / 315 C. Benzopyrans / 317 D. Quinolines / 321 I. Antimalarial Compounds / 321 CONTENTS Xi 2. Other Quinolines / 324 3. Antibacterial Quinolones / 330 E. Isoquinoline and Its Derivatives / 336 2. Compounds with Two Heteroatoms / 340 A. Benzodioxans / 340 B. Cinnolines and Phthalazines / 343 C. Quinazolines / 346 D. Quinazolones / 351 3. Compounds with Three Heteroatoms / 356 12 SEVEN-MEMBERED HETEROCYCLIC RINGS FUSED TO BENZENE 362 1. Compounds with One Heteroatom / 362 2. Compounds with Two Heteroatoms / 364 A. Benzodiazepine Anxiolytic Agents / 364 B. Other Seven-Membered Heterocycles Fused to a Benzene Ring / 372 13 HETEROCYCLES FUSED TO TWO BENZENE RINGS 379 1. Compounds with One Heteroatom / 379 A. Derivatives of Dibenzopyran and Dibenzoxepin / 379 B. Dibenzo Heterocycles with One-Ring Nitrogen Atom / 383 C. Dibenzo Heterocycles with One Sulfur Atom / 388 2. Compounds with Two Heteroatoms / 392 A. Phenothiazines / 392 B. Dibenzodiazepines, Dibenzoxazepines, and a Dibenzothiazepine / 395 C. Azadibenzodiazepines / 398 14 BETA-LACTAM ANTIBIOTICS 401 1. Penicillins / 402 2. Cephalosporins / 413 3. Monobactams / 426 Xii CONTENTS 15 HETEROCYCLES FUSED TO OTHER HETEROCYCLIC RINGS 431 1. Two Fused Five-Membered Rings / 431 2. Five-Membered Heterocycles Fused to Six-Membered Rings / 434 A. Compounds with Two Heleroatoms / 434 B. Compounds with Three Heteroatoms / 438 C. Compounds with Four Heteroatoms / 442 A Purities / 442 2. Comounds with an N,N-Linkage / 448 3. Two Fused Six-Membered Rings / 450 A. Compounds Related to Methotrexate / 450 B. Other Fused Heterocyclic Compounds / 453 4. Heterodiazepines / 457 5. Heterocyclic Compounds with Three or More Rings / 459 CROSS INDEX OF COMPOUNDS 469 REACTION INDEX 477 SUBJECT INDEX 493.
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