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Contents
Preface v
Acknowledgements vii
Chapter 1 Introduction to Pharmaceutical Chemistry of Natural Products 1
_ Introduction 1
_ Drug Discovery from Natural Products 2
_ Nomenclature 3
_ Classifi cation of Natural Products 3
_ Identifi cation of Natural Products 6
_ Techniques Involved in Natural Product Lead Discovery 6
_ Natural Products as Pharmacological Tools 8
Chapter 2 Carbohydrates 11
_ Introduction 11
_ Classifi cation of Carbohydrates 12
_ Qualitative Chemical Tests for Carbohydrates 14
_ Monosaccharides 16
_ Confi guration of Monosaccharides 16
_ Ascending and Descending in Monosaccharides 18
_ Chemical Reactions of Monosaccharides 20
_ Ring Size of Monosaccharides 27
_ Ring structure of aldoses (glucose) 28
_ Ring structure of ketoses (fructose) 39
_ Conformations of Monosaccharides 42
_ Monosaccharides of Pharmaceutical Importance 42
_ Glucose 42
_ Fructose 44
_ Disaccharides 47
_ Biological Importance of Disaccharides 47
_ Classifi cation and Nomenclature of Disaccharides 47
_ Determination of the Structure of Disaccharides 49
_ Disaccharides of Pharmaceutical Importance 49
_ Sucrose 49
_ Lactose 53
_ Maltose 55
_ Trehalose 58
_ Trisaccharides 60
_ Gentianose 60
_ Tetrasaccharides 61
_ Stachyose 61
_ Polysaccharides 62
_ Classifi cation and Nomenclature of Polysaccharides 62
_ Polysaccharides of Pharmaceutical Importance 63
_ Starch 63
Chapter 3 Glycosides 73
_ Introduction 73
_ Classifi cation of Glycosides 74
_ Qualitative Chemical Tests for Glycosides 80
_ Isolation of Glycosides 81
_ Structural Determination of Glycosides 82
_ Glycosides of Pharmaceutical Importance 83
_ Salicin 83
_ Ruberythric acid 84
_ Arbutin 86
_ Sinigrin 88
_ Amygdalin 89
Chapter 4 Amino Acids, Peptides and Proteins 93
_ Amino Acids 93
_ Nomenclature of Amino Acids 94
_ Qualitative Chemical Tests for Amino Acids 94
_ Classifi cation of Amino Acids 95
_ Isolation and Separation of Amino Acids from Proteins 96
_ Synthesis of Amino Acids 97
_ General Physical and Chemical Properties of Amino Acids 102
_ Peptides 110
_ Classifi cation of Peptides 111
_ Synthesis of Peptides 111
_ General Principles of Peptide Synthesis 112
_ General Methods of Peptide Synthesis 115
_ Structure of Peptides 117
_ N-Terminal (Amino-end) degradation 118
_ C-Terminal (Carboxyl-end) degradation 120
_ Proteins 122
_ Biological Functions 122
_ Classifi cation of Proteins 122
_ Qualitative Chemical Tests for Proteins 124
_ Structure of Proteins 125
_ Proteins of Pharmaceutical Importance 132
_ Glutathione 132
_ Oxytocin 135
_ Thyroxine 138
_ Insulin 142
Chapter 5 Alkaloids 149
_ Introduction 149
_ Nomenclature of Alkaloids 150
_ Classifi cation of Alkaloids 150
_ Qualitative Chemical Tests for Alkaloids 158
_ Isolation or Production of Alkaloids 159
_ Determination of Molecular Structure of Alkaloids: General Methods 160
_ Molecular Formula Determination 160
_ Hydrolysis 160
_ Determination of Unsaturation 160
_ Functional Group Determination 160
_ Degradation of Alkaloids 164
_ Physical Methods in Conjunction with Chemical Methods 169
_ Synthesis 170
_ Alkaloids of Pharmaceutical Importance 170
_ Atropine 172
_ Morphine 177
_ Quinine 186
_ Papaverine 194
_ Emetine 199
_ Ephedrine 205
_ Ergotamine 207
_ Reserpine 214
_ Strychnine 222
_ Colchicine 232
_ Piperine 238
_ Nicotine 240
Chapter 6 Steroids and Hormones 249
_ Steroids 249
_ Nomenclature of Steroids 251
_ Stereochemistry 253
_ Qualitative Chemical Tests for Steroids 254
_ Sterols 254
_ Cholesterol 255
_ Lanosterol 256
_ Stigmasterol 257
_ Ergosterol 257
_ Miscellaneous Sterols 258
_ Structural Elucidation of Cholesterol 258
_ Bile acids 268
_ 5β-Cholanic Acid 270
_ 5α-Cholanic Acid 271
_ Functions of Bile Acids 271
_ Saponins and Sapogenins 272
_ Steroidal Saponins 272
_ Synthesis of Diosgenin 274
_ Pentacyclic Triterpenoid Saponins 276
_ Steroidal Alkaloids 277
_ Cardiac Steroids or Cardiotonic Glycosides 278
_ Hormones 282
_ Classifi cation 283
_ Sex Hormones 283
_ Biosynthesis of Sex Steroid Hormones 284
_ Androgens (Male Sex Hormones) 285
_ Biological Activities of Androgens 285
_ Therapeutic Uses of Anabolic Androgenic Steroids 286
_ Androgens of Pharmaceutical Importance 286
_ Androgesterone 286
_ Dehydroepiandrosterone 288
_ Testosterone 289
_ Methyl Testosterone 292
_ Fluoxymesterone 292
_ SAR of Androgens 293
_ Oestrogens 295
_ Isolation of Oestrogens 296
_ Biological Activities of Oestrogens 296
_ Metabolism of Oestrogens 297
_ Therapeutic Uses of Oestrogens 297
_ Classifi cation of Oestrogens 298
_ Oestrogens of Pharmaceutical Importance 300
_ Oestrone 300
_ Oestriol 301
_ Oestradiol 303
_ 17α-Ethinyloestradiol 305
_ Chemical Relationship Between Oestrone, Oestriol and Oestradiol 306
_ Nonsteroidal Oestrogens or Artifi cial Hormones 308
_ Stilboesterol 308
_ Hexoestrol 310
_ Dienoestrol 310
_ Benzoestrol 312
_ Structure–Activity Relationship (SAR) of Oestrogens 313
_ Corpus Luteum Hormones or Gestogens or Progestins 315
_ Metabolism of Progesterone 316
_ Biological Activities of Progestins 316
_ Therapeutic Uses of Progestins 316
_ Classifi cation of Progesterones 317
_ Progestins of Pharmaceutical Importance 318
_ Progesterone 318
_ Progesterone derivatives 322
_ Structure–Activity Relationship (SAR) of Progesterones 324
_ Hormonal Contraceptives 326
_ Oral Contraceptives 326
_ Corticosteroids (Adrenal Cortical Hormones) 327
_ Biological Effects of Glucocorticoids 327
_ Biosynthesis of the Adrenocorticoids from Cholesterol 328
_ Therapeutic Uses of Glucocorticoids 329
_ Classifi cation of Corticosteroids 329
_ Corticosteroids of Pharmaceutical Importance 333
_ Cortisone 333
_ Cortisol (or) Hydrocortisone 334
_ Aldosterone 337
_ Prednisolone 338
_ Dexamethasone 340
_ SAR of Corticosteroids 341
Chapter 7 Terpenoids
349_ Introduction 349
_ Isolation of Terpenoids 352
_ Classifi cation of Terpenoids 353
_ Isoprene Rule and Special Isoprene Rule 361
_ General Methods for the Elucidation of Structure of Terpenoids 363
_ Hemiterpenoids 366
_ Monoterpenoids or Terpenes 367
_ Acyclic Monoterpenoids 367
_ Citral 367
_ Citronellal 371
_ Citronellol 373
_ Geraniol 374
_ Nerol 376
_ Linalool 377
_ Myrcene 378
_ Ocimene 378
_ Lavundulol 378
_ Cyclization Reactions of Acyclic Monoterpenoids 379
_ Monocyclic Monoterpenoids 381
_ Limonene 381
_ α-Terpineol 384
_ 1,8-cineol 389
_ Menthol and Menthone 390
_ Pulegone 392
_ Carvone 393
_ Ionones 397
_ Bicyclic Monoterpenoids 399
_ α-Pinene 399
_ Camphor 404
_ Borneol and Isoborneol 409
_ Camphene 410
_ Fenchone 410
_ Sesquiterpenoids 410
_ Acyclic Sesquiterpenoids 410
_ Farnesol 411
_ Monocyclic Sesquiterpenoids 413
_ Zingiberene 414
_ Bicyclic Sesquiterpenoids 417
_ Cadinene 417
_ Miscellaneous Sesquiterpenoids 418
_ Artimisinin 418
_ Gossypol and related compounds 418
_ Diterpenoids 419
_ Phytol 419
_ Vitamin A 419
_ Abietic Acid 420
_ Ginkolides 420
_ Taxol 420
_ Triterpenoids 421
_ Squalene 421
_ Lanosterol and Euphol 422
_ Amyrins 422
_ Tetraterpenoids 422
_ Polyterpenoids 423
Chapter 8 Flavonoids 427
_ Introduction 427
_ Isolation of Flavones 428
_ Structural Elucidation of Flavones 429
_ Flavonol 431
_ Structural Elucidation of Flavonol 432
_ Quercetin 434
_ Structural Elucidation of Quercetin 434
_ Isofl avones 437
_ Structural Elucidation of Isofl avones 438
Chapter 9 Vitamins 441
_ Introduction 441
_ Nomenclature of Vitamins 442
_ Classifi cation of Vitamins 443
_ Sources of Vitamins and Their Defi ciency Diseases 445
_ Vitamin A 446
_ Vitamin D 463
_ Vitamin E (Tocopherols) 474
_ Vitamin K 490
_ Vitamin B Complex 503
_ Vitamin B1 503
_ Vitamin B2 514
_ Vitamin B3 526
_ Vitamin B5 533
_ Vitamin B9 or Vitamin Bc or Folic Acid 540
_ Vitamin B6 or Pyridoxine 548
_ Vitamin B12 (Cyanocobalamin) 560
_ Vitamin C (Ascorbic Acid) 571
_ Vitamin-Like Compounds 588
_ PABA 588
_ Choline 588
_ Carnitine 589
_ Lipoic Acid or Vitamin Bt 590
Chapter 10 Antibiotics 593
_ Introduction 593
_ Historical Background 594
_ Spectrum of Activity of Chemotherapeutic Agents 594
_ Classifi cation Based on Mechanism of Action 596
_ Classifi cation Based on Chemical Structure 597
_ Penicillins 597
_ Introduction 597
_ Nomenclature 598
_ Production of Penicillins 598
_ Isolation of Penicillins 599
_ Chemical Degradation of Penicillins 600
_ Structural Elucidation of Penicillins 601
_ Classifi cation 606
_ Structure–Activity Relationship (SAR) of Penicillins 610
_ Cephalosporins 611
_ Introduction 611
_ Nomenclature 612
_ Degradation of Cephalosporins 613
_ Structural Elucidation of Cephalosporins 614
_ Classifi cation of Cephalosporins 619
_ Adverse Effects of Cephalosporins 623
_ Uses of Cephalosporins 623
_ SAR of Cephalosporins 623
_ Aminoglycoside antibiotics 625
_ Introduction 625
_ Production of Streptomycin 625
_ Isolation of Streptomycin 626
_ Streptomycin and Dihydrostreptomycin 626
_ Structural Elucidation of Streptomycin 627
_ Gentamycins 633
_ Neomycin 633
_ Kanamycin 634
_ Amikacin 635
_ Tobramycin 635
_ Netilmicin 636
_ SAR of Aminoglycoside Antibiotics 636
_ Tetracyclines 637
_ Introduction 637
_ Classifi cation of Tetracyclines 638
_ Structural Elucidation of Oxytetracycline 640
_ SAR of Tetracyclines 647
_ Chloramphenicol or Chloromycetin 649
_ Introduction 649
_ Structural Elucidation of Chloramphenicol 650
_ SAR of Chloramphenicol 653
_ Polypeptide antibiotics 654
_ Introduction 654
_ Bacitracin 654
_ Polymyxin 655
_ Lincomycins 655
Chapter 11 Purines, Pyrimidines and Nucleic Acids 659
_ Introduction 659
_ Purines 659
_ Classifi cation of Purines 660
_ Purine 661
_ Adenine 664
_ Guanine 666
_ Uric Acid 667
_ Xanthine 673
_ Methylxanthines 674
_ Caffeine 675
_ Theobromine 678
_ Theophylline 680
_ Hypoxanthine 682
_ Relationship Between Uric Acid and Xanthine Bases 683
_ Pyrimidines 684
_ Uracil 684
_ Thymine 686
_ Cytosine 687
_ 5-Methyl Cytosine 688
_ 5-Hydroxy Methyl Cytosine 689
_ NUCLEIC ACIDS 690
_ Classifi cation of Nucleic Acids 690
_ Functions of Nucleic Acids 691
_ Components of Nucleic Acids 691
_ Nucleosides 692
_ Nucleotides 694
_ Structural Elucidation of Nucleic Acids 696
_ Internucleotide Bond in RNA 713
_ Internucleotide Bond in DNA 714
_ Structure of DNA 715
_ Structure of RNA 719
_ Types of RNA 720
_ Differences Between DNA and RNA 722
Chapter 12 Enzymes
725_ Introduction 725
_ Nomenclature and Classifi cation of Enzymes 726
_ Oxidoreductase 727
_ Transferase 727
_ Hydrolase 728
_ Lyase 728
_ Isomerase 728
_ Ligase 729
_ Qualitative Chemical Tests for Enzymes 729
_ Chemical Nature of Enzymes 730
_ Effi ciency of Enzymes 730
_ Specifi city of Enzymes 731
_ Stereospecifi city or Optical Specifi city 731
_ Reaction Specifi city 732
_ Substrate Specifi city 732
_ Theories of Enzyme Action 732
_ Lock and Key Model 733
_ Induced Fit Theory 733
_ Substrate Strain Theory 734
_ Mechanism of Enzyme Action 734
_ Coenzymes 735
_ Enzymatic Catalysis 738
_ Catalysis by Proximity and Orientation 738
_ Acid–Base Catalysis 738
_ Catalysis by Strain 739
_ Covalent Catalysis 739
_ Enzyme Inhibition 740
_ Reversible Inhibition 741
_ Irreversible Inhibition 743
Chapter 13 Lipids 745
_ Introduction 745
_ Classifi cation of Lipids 746
_ Simple Lipids (Fats and Oils) 747
_ Differences Between Fats and Oils 747
_ Nomenclature of Fats 748
_ Extraction of Fats 749
_ Physical and Chemical Properties of Fats and Oils 749
_ Analysis of Oils and Fats 751
_ Fatty Acids 754
_ Nomenclature of Fatty Acids 754
_ Classifi cation of Fatty Acids 755
_ Waxes 757
_ Common Waxes 757
_ Compound Lipids/Complex Lipids 758
_ Lecithins 758
_ Cephalins 759
_ Plasmalogens 759
_ Sphingomyelins 760
_ Glycolipids, Galactolipids and Cerebrosides 760
_ Derived Lipids 761
_ Sterols 762
_ Cholesterol 762
_ Lanosterol 763
_ Stigmasterol 763
_ Ergosterol 764
Index
767