Chemistry for Pharmacy Students: General, Organic and Natural Product Chemistry

ISBN-13: 9781119394433 / Angielski / Miękka / 2019 / 536 str.

Lutfun Nahar; Satyajit Sarker

Spis treści

Preface to the second edition xvPreface to the first edition xviiChapter 1: Introduction 11.1 Role of Chemistry in Modern Life 11.2 Solutions and Concentrations 41.3 Suspension, Colloid and Emulsion 61.4 Electrolytes, Nonelectrolytes and Zwitterions 71.5 Osmosis and Tonicity 81.6 Physical Properties of Drug Molecules 101.6.1 Physical State 101.6.2 Melting Point and Boiling Point 101.6.3 Polarity and Solubility 111.7 Acid-Base Properties and pH 131.7.1 Acid-Base Definitions 141.7.2 Electronegativity and Acidity 181.7.3 Acid-Base Properties of Organic Functional Groups 191.7.4 pH, pOH and pKa Values 221.7.5 Acid-Base Titration: Neutralization 301.8 Buffer and its Use 321.8.1 Common Ion Effects and Buffer Capacity 34Chapter 2: Atomic Structure and Bonding 372.1 Atoms, Elements and Compounds 372.2 Atomic Structure: Orbitals and Electronic Configurations 392.3 Chemical Bonding Theories: Formation of Chemical Bonds 432.3.1 Lewis Structures 432.3.2 Resonance and Resonance Structures 472.3.3 Electronegativity and Chemical Bonding 482.3.4 Various Types of Chemical Bonding 492.4 Bond Polarity and Intermolecular Forces 542.4.1 Dipole-Dipole Interactions 542.4.2 van der Waals Forces 552.4.3 Hydrogen Bonding 562.5 Hydrophilicity and Lipophilicity 572.6 Significance of Chemical Bonding in Drug-Receptor Interactions 602.7 Significance of Chemical Bonding in Protein-Protein Interactions 632.8 Significance of Chemical Bonding in Protein-DNA Interactions 63Chapter 3: Stereochemistry 653.1 Stereochemistry: Definition 663.2 Isomerism 663.2.1 Constitutional Isomers 663.2.2 Stereoisomers 673.3 Stereoisomerism of Molecules with More than One Stereocentre 823.3.1 Diastereomers and Meso Structures 823.3.2 Cyclic Compounds 843.3.3 Geometrical Isomers of Alkenes and Cyclic Compounds 853.4 Significance of Stereoisomerism in Determining Drug Action and Toxicity 883.5 Synthesis of Chiral Molecules 913.5.1 Racemic Forms 913.5.2 Enantioselective Synthesis 923.6 Separation of Stereoisomers: Resolution of Racemic Mixtures 933.7 Compounds with Stereocentres Other than Carbon 943.8 Chiral Compounds that Do Not Have Four Different Groups 94Chapter 4: Organic Functional Groups 974.1 Organic Functional Groups: Definition and Structural Features 974.2 Hydrocarbons 1004.3 Alkanes, Cycloalkanes and Their Derivatives 1004.3.1 Alkanes 1004.3.2 Cycloalkanes 1084.3.3 Alkyl Halides 1114.3.4 Alcohols 1194.3.5 Ethers 1254.3.6 Thiols 1294.3.7 Thioethers 1314.3.8 Amines 1344.4 Carbonyl Compounds 1404.4.1 Aldehydes and Ketones 1404.4.2 Carboxylic acids 1484.4.3 Acid Chlorides 1544.4.4 Acid Anhydrides 1554.4.5 Esters 1574.4.6 Amides 1604.4.7 Nitriles 1634.5 Alkenes and their Derivatives 1644.5.1 Nomenclature of Alkenes 1654.5.2 Physical Properties of Alkenes 1664.5.3 Structure of Alkenes 1674.5.4 Industrial uses of Alkenes 1674.5.5 Preparations of Alkenes 1684.5.6 Reactivity and Stability of Alkenes 1684.5.7 Reactions of Alkenes 1694.6 Alkynes and their Derivatives 1694.6.1 Nomenclature of Alkynes 1704.6.2 Structure of Alkynes 1704.6.3 Acidity of Terminal Alkynes 1714.6.4 Heavy Metal Acetylides: Test for Terminal Alkynes 1714.6.5 Industrial Uses of Alkynes 1724.6.6 Preparations of Alkynes 1724.6.7 Reactions of Alkynes 1724.6.8 Reactions of Metal Alkynides 1744.7 Aromatic Compounds and their Derivatives 1744.7.1 History 1754.7.2 Definition: Hückel's Rule 1754.7.3 General Properties of Aromatic Compounds 1754.7.4 Classification of Aromatic Compounds 1764.7.5 Pharmaceutical importance of Aromatic Compounds: Some Examples 1774.7.6 Structure of Benzene: Kekulé Structure of Benzene 1794.7.7 Nomenclature of Benzene Derivatives 1834.7.8 Electrophilic Substitution of Benzene 1844.7.9 Alkylbenzene: Toluene 1904.7.10 Phenols 1924.7.11 Aromatic Amines: Aniline 1994.7.12 Polycyclic Benzenoids 2074.8 Importance of Functional Groups in Determining Drug Actions and Toxicity 2094.8.1 Structure-Activity Relationships of Sulpha Drugs 2104.8.2 Structure-Activity Relationships of Penicillins 2114.8.3 Paracetamol Toxicity 2134.9 Importance of Functional Groups in Determining Stability of Drugs 213Chapter 5: Organic Reactions 2155.1 Types of Organic Reactions Occur with Functional Groups 2155.2 Reaction Mechanisms and Types of Arrow in Chemical Reactions 2165.3 Free Radical Reactions: Chain Reactions 2175.3.1 Free Radical Chain Reaction of Alkanes 2175.3.2 Relative Stabilities of Carbocations, Carbanions, Radicals and Carbenes 2195.3.3 Allylic Bromination 2215.3.4 Radical Inhibitors 2225.4 Addition Reactions 2235.4.1 Electrophilic Additions to Alkenes and Alkynes 2235.4.2 Symmetrical and Unsymmetrical Addition to Alkenes and Alkynes 2265.4.3 Nucleophilic Addition to Aldehydes and Ketones 2405.5 Elimination Reactions: 1,2-Elimination or ß-Elimination 2545.5.1 E1 Reaction or First Order Elimination 2555.5.2 E2 Reaction or Second Order Elimination 2565.5.3 Dehydration of Alcohols 2575.5.4 Dehydration of Diols: Pinacol Rearrangement 2595.5.5 Base-Catalysed Dehydrohalogenation of Alkyl Halides 2605.6 Substitution Reactions 2655.6.1 Nucleophilic Substitutions 2665.6.2 Nucleophilic Substitutions of Alkyl Halides 2735.6.3 Nucleophilic Substitutions of Alcohols 2765.6.4 Nucleophilic Substitutions of Ethers and Epoxides 2825.6.5 Nucleophilic Acyl Substitutions of Carboxylic Acid Derivatives 2865.6.6 Substitution Versus Elimination 2935.7 Electrophilic Substitutions 2945.7.1 Electrophilic Substitution of Benzene 2945.8 Hydrolysis 3005.8.1 Hydrolysis of Carboxylic Acid Derivatives 3005.9 Oxidation-Reduction Reactions 3055.9.1 Oxidizing and Reducing Agents 3055.9.2 Oxidation of Alkenes 3055.9.3 Oxidation of Alkynes 3075.9.4 Hydroxylation of Alkenes 3075.9.5 Oxidative Cleavage of syn-Diols 3085.9.6 Ozonolysis of Alkenes 3085.9.7 Ozonolysis of Alkynes 3095.9.8 Oxidation of Alcohols 3095.9.9 Oxidation of Aldehydes and Ketones 3115.9.10 Baeyer-Villiger Oxidation of Aldehydes or Ketones 3125.9.11 Reduction of Alkyl Halides 3125.9.12 Reduction of Organometallics 3125.9.13 Reduction of Alcohols via Tosylates 3135.9.14 Reduction of Aldehydes and Ketones 3135.9.15 Clemmensen Reduction 3155.9.16 Wolff-Kishner Reduction 3165.9.17 Reduction of Acid Chlorides 3165.9.18 Reduction of Esters 3175.9.19 Hydride Reduction of Carboxylic Acids 3185.9.20 Reduction of Oximes or Imine Derivatives 3185.9.21 Reduction of Amides, Azides and Nitriles 3195.9.22 Reductive Amination of Aldehydes and Ketones 3205.10 Pericyclic Reactions 3205.10.1 Diels-Alder Reaction 3205.10.2 Essential Structural Features for Dienes and Dienophiles 3215.10.3 Stereochemistry of the Diels-Alder Reaction 3225.10.4 Sigmatropic Rearrangements 3235.10.5 Hydrogen Shift 3235.10.6 Alkyl Shift: Cope Rearrangement 3245.10.7 Claisen Rearrangement 324Chapter 6: Heterocyclic Compounds 3276.1 Heterocyclic Compounds and their Derivatives 3276.1.1 Medicinal Importance of Heterocyclic Compounds 3286.1.2 Nomenclature of Heterocyclic Compounds 3296.1.3 Physical Properties of Heterocyclic Compounds 3316.2 Pyrrole, Furan and Thiophene: Unsaturated Heterocycles 3326.2.1 Physical Properties of Pyrrole, Furan and Thiophene 3336.2.2 Preparations of Pyrrole, Furan and Thiophene 3336.2.3 Reactions of Pyrrole, Furan and Thiophene 3356.3 Pyridine 3396.3.1 Physical Properties of Pyridine 3396.3.2 Preparations of Pyridine 3406.3.3 Reactions of Pyridine 3406.4 Oxazole, Imidazole and Thiazole 3426.4.1 Physical Properties of Oxazole, Imidazole and Thiazole 3436.4.2 Preparations of Oxazole, Imidazole and Thiazole 3446.4.3 Reactions of Oxazole, Imidazole and Thiazole 3456.5 Isoxazole, Pyrazole and Isothiazole 3466.5.1 Physical Properties of Isoxazole, Pyrazole and Isothiazole 3486.5.2 Preparations of Isoxazole, Pyrazole and Isothiazole 3486.5.3 Reactions of Isoxazole, Pyrazole and Isothiazole 3486.6 Pyrimidine 3496.6.1 Physical Properties of Pyrimidine 3506.6.2 Preparations of Pyrimidine 3506.6.3 Reactions of Pyrimidine 3516.7 Purine 3526.7.1 Physical Properties of Purine 3536.7.2 Preparations of Purine 3536.7.3 Reactions of Purine 3536.8 Quinoline and Isoquinoline 3546.8.1 Physical Properties of Quinoline and Isoquinoline 3546.8.2 Preparations of Quinoline and Isoquinoline 3556.8.3 Reactions of Quinoline and Isoquinoline 3576.9 Indole 3586.9.1 Physical Properties of Indole 3596.9.2 Preparations of Indole 3596.9.3 Reactions of Indole 3606.9.4 Test for Indole 361Chapter 7: Nucleic Acids 3637.1 Nucleic Acids 3637.1.1 Synthesis of Nucleosides and Nucleotides 3657.1.2 Structure of Nucleic Acids 3667.1.3 Nucleic Acids and Heredity 3707.1.4 DNA Fingerprinting 3737.2 Amino Acids and Peptides 3737.2.1 Fundamental Structural Features of an Amino acid 3767.2.2 Essential Amino Acids 3767.2.3 Glucogenic and Ketogenic Amino Acids 3777.2.4 Amino Acids in Human Body 3777.2.5 Acid-Base Properties of Amino Acids 3787.2.6 Isoelectric Points of Amino Acids and Peptides 378Chapter 8: Natural Product Chemistry 3818.1 Introduction to Natural Products 3818.1.1 Natural Products 3818.1.2 Natural Products in Medicine 3828.1.3 Drug Discovery and Natural Products 3858.2 Alkaloids 3908.2.1 Properties of Alkaloids 3918.2.2 Classification of Alkaloids 3918.2.3 Tests for Alkaloids 4108.3 Carbohydrates 4108.3.1 Classification of Carbohydrates 4118.3.2 Stereochemistry of Sugars 4148.3.3 Cyclic Structures of Monosaccharides 4158.3.4 Acetal and Ketal Formation in Sugars 4168.3.5 Oxidation, Reduction, Esterification and Etherification of Monosaccharides 4178.3.6 Pharmaceutical Uses of Monosaccharides 4208.3.7 Disaccharides 4208.3.8 Polysaccharides 4238.3.9 Miscellaneous Carbohydrates 4268.3.10 Cell Surface Carbohydrates and Blood Groupings 4288.4 Glycosides 4298.4.1 Biosynthesis of Glycosides 4308.4.2 Classification 4308.4.3 Test for Hydrocyanic Acid (HCN) 4328.4.4 Pharmaceutical Uses and Toxicity 4328.4.5 Anthracene/Anthraquinone Glycosides 4338.4.6 Isoprenoid Glycosides 4368.4.7 Iridoid and Secoiridoid Glycosides 4408.5 Terpenoids 4428.5.1 Classification 4428.5.2 Biosynthesis of Terpenoids 4438.5.3 Monoterpenes 4458.5.4 Sesquiterpenes 4468.5.5 Diterpenes 4558.5.6 Triterpenes 4618.5.7 Tetraterpenes 4658.6 Steroids 4668.6.1 Structures of Steroids 4678.6.2 Stereochemistry of Steroids 4688.6.3 Physical Properties of Steroids 4688.6.4 Types of Steroid 4698.6.5 Biosynthesis of Steroids 4718.6.6 Synthetic Steroids 4728.6.7 Functions of Steroids 4738.7 Phenolics 4768.7.1 Phenylpropanoids 4778.7.2 Coumarins 4788.7.3 Flavonoids and Isoflavonoids 4818.7.4 Lignans 4868.7.5 Tannins 489Index 493

O autorze

Lutfun Nahar, BSc (Hons), PhD, MRSC, FHEA, is an Honorary Lecturer, and actively involved in research at the Faculty of Science at Liverpool John Moores University, UK. She has published well over 350 peer-reviewed scientific papers, invited reviews, abstracts, books, and book chapters in the areas of Synthetic Organic Medicinal and Natural Products Chemistry. She is the Managing Editor of the Wiley journal, Phytochemical Analysis. Her scientific profile has been published in every edition of the Marquis "Who's Who in the World" since 2009, and "Who's Who in Science and Engineering" since 2010.Satyajit Sarker BPharm (Hons), MPharm, PhD, FHEA, is a Professor of Pharmacy, and the Director of School of Pharmacy and Biomolecular Sciences at Liverpool John Moores University, UK. He is the President of the Phytochemical Society of Europe, and the Editor-in-Chief of the Wiley journal, Phytochemical Analysis. He has over 520 publications to his credit. His scientific profile has been published in every edition of the Marquis "Who's Who in the World" since 2010.