Syntheses of Organic Medicinal Compounds

Antihypertensive agents 77 Drugs acting at or near post-ganglionic nerve endings; Adrenergic neuron blocking agents; Drugs acting directly on smooth m...

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Syntheses of Organic Medicinal Compounds

M. P. S. Ishar Abdul Faruk

Alpha Science International Ltd. Oxford, U.K.

Contents Preface

vii

1. Introduction Aldol condensation; Knoevenagel Condensation; Michael Addition; AdditionElimination reactions; Mannich reaction; Benzoin Condensation; DieckmannCondensation; Reformatsky reaction; Wurtz reaction; Wittig reaction; Sulfur ylides; Synthesis of Oxiranes; Synthesis of Cyclopropane; Synthesis of Aziridines; Synthesis of Azitidine; Electrophilic Aromatic Substitution; Aromatic Nucleophilic Substitutions; Rearrangements; Cannizzaro reaction; Etherification and de-Etherification; Oppenauer Oxidation and MeerweinPonndrof-Verley reduction; Organometallic reagents; Preparation of Esters and Amides; Protection (blocking) and Deprotection (de-blocking) of functional groups; Fischer-Indole Synthesis; Hantzsch Pyridine Synthesis; Hantzsch Synthesis of Pyrrole; Knorr Pyrrole Synthesis; Skraup Synthesis of quinolines; Dehydrogenation by high potential quinones like Chloranil and DQQ; Heck reaction

1

2. Neuroleptics Phenothiazines; Thioxanthenes; Butyrophenones; Dibenzazepines; Indole derivatives; Diphenylbutylpiperidines and related compounds; Benzamides; Benzoquinolizines

36

3. Anxiolytics Benzodiazepines; Diphenylmethanes; Propanediol carbamates; Azaspirodecanediones

55

4. Hypnotics and Sedatives Barbiturates; Benzodiazepines; Carbamates; Piperidinediones

62

5. Local Anesthetics Benzoic acid derivatives; Anilides; Aminobenzoicacid derivatives; Miscellaneous agents

65

6. Antihypertensive agents Drugs acting at or near post-ganglionic nerve endings; Adrenergic neuron blocking agents; Drugs acting directly on smooth muscles; Centrally acting sympathomimetic agents; p-Adrenergic blocking agents; Miscellaneous Hypotensive Drugs

77

x Contents 7. Antilipidemic agents Clofibrate; Clofenpyride; Clofibride; Etofibrate; Etofylline Clofibrate; Pyridoxine Clofibrate; Pirifibrate; Simfibrate; Tiafibrate; Timofibrate; Lifibrate; Ciprofibrate; Benzafib.rate; Gemfibrozil; Probucol; Nicotinic acid; D-thyroxine; Liothyronine; L-triiodothyronine; Thyromedan; Fluvastatin

8. Anti-coagulants; Coagulants and Anti-platelet agents

91

98

Anti-coagulants Coumarin derivatives; 1,3-Indandione derivatives Coagulants Carbazochrome Salicylate; Negatol Antiplatelet agents Acetylsalicylic acid; Sulfinpyrazone: Dipyridamole 9. Hypoglycemic agents Sulfonyl ureas

104

10.

Diuretics Mercurials; Phenoxy acetic acid derivatives; Pteridines and Pyrazinoylguanidines; Anti-harmone diuretics; Sulfonamides; Benzothiadiazines (a) 1,2,4Benzothiadiazine; (b) 3,4-dihydro 2H-1,2,4-Benzothiadiazines Quinazoline derivatives; Sulfamyl benzoic acid derivatives and related compounds

108

11.

Non Steroidal Anti-inflammatory Drugs (NSAIDS) Salicylic acid derivatives; Aniline and p-Aminophenol derivatives; 5-Pyrazolone derivatives; 3,5-Pyrazolidinedione derivatives; N-Arylanthranilic acid (Fenamates); Aryl and Heteroaryl acetic acid derivatives; Pyrroleacetic acid derivatives; 2-Phenylpropionic acid derivatives; Naphthylacetic acid derivatives; Miscellaneous agents

122

12. Antihistaminic agents Hj Antagonists Aminoalkyl ether derivatives; Ethylenediamine derivatives; Propylamine derivatives; Phenothiazine derivatives; Piperazine derivatives; Miscellaneous agents H2 Antagonists

140

13. Antimalarials Cinchona alkaloid; 4-Aminoquinolines; 9-Aminoacridines; 8-Aminoquinolines; Pyrimidines; Biguanides; Sulfones

157

14. Anti-viral agents

169

Agents interfering with viral nucleic acid replication; Agents interfering with viral nucleic acid replication; Agents affecting translation on cell ribosomes 15. Antifungal agents Synthetic antifungal agents; Antifungal Antibiotics

174

16. Antiprotozoal agents

180

17. Anthelmintics

183

Contents xi 18. Antitubercular agents

192

19. Antineoplastic agents Alkylating agents; Antimetabolites; DNA-Intercalating agents

195

20. Sulfonamides Highly absorbed Sulfonamides; Poorly absorbed Sulfonamide (for intestinal infections); Sulfonamide for topical use

206

21. Antibiotics Natural penicillins; Semisynthetic penicillins; Cephalosporins; Tetracyclines; Antibiotics derived from aminoacids; Quinolone or Fluroquinolone antibacterials

214

22. Steroids Testosterone; Progesterone; Conversions of estrogens; Ethinylestradiol; Mestranol; Diethylstilbestrol; Dienestrol; Chlorotrianisene; Hexestrol; Glucocorticoids

240

23. Vitamins Lipid soluble vitamins; Water soluble vitamins

255

24. Index

266