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Chemistry for Pharmacy Students: General, Organic and Natural Product Chemistry, 2nd Edition

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Chemistry for Pharmacy Students: General, Organic and Natural Product Chemistry, 2nd Edition

Lutfun Nahar, Satyajit Sarker

ISBN: 978-1-119-39443-3 September 2019 496 Pages

Description

Introduces the key areas of chemistry required for all pharmacy degree courses and focuses on the properties and actions of drug molecules

This new edition provides a clear and comprehensive overview of the various areas of general, organic, and natural products chemistry (in relation to drug molecules). Structured to enhance student understanding, it places great emphasis on the applications of key theoretical aspects of chemistry required by all pharmacy and pharmaceutical science students. This second edition particularly caters for the chemistry requirements in any ‘Integrated Pharmacy Curricula’, where science in general is meant to be taught ‘not in isolation’, but together with, and as a part of, other practice and clinical elements of the course.

Chemistry for Pharmacy Students: General, Organic and Natural Product Chemistry, 2nd Edition is divided into eight chapters. It opens with an overview of the general aspects of chemistry and their importance to modern life, with emphasis on medicinal applications. The text then moves on to discuss the concepts of atomic structure and bonding and the fundamentals of stereochemistry and their significance to pharmacy in relation to drug action and toxicity. Various aspects of organic functional groups, organic reactions, heterocyclic chemistry, nucleic acids and their pharmaceutical importance are then covered in subsequent chapters, with the final chapter dealing with drug discovery and development, and natural product chemistry.

  • Provides a student-friendly introduction to the main areas of chemistry required by pharmacy degree courses
  • Written at a level suitable for non-chemistry students in pharmacy, but also relevant to those in life sciences, food science, and the health sciences
  • Includes learning objectives at the beginning of each chapter
  • Focuses on the physical properties and actions of drug molecules

Chemistry for Pharmacy Students: General, Organic and Natural Product Chemistry, 2nd Edition is an essential book for pharmacy undergraduate students, and a helpful resource for those studying other subject areas within pharmaceutical sciences, biomedical sciences, cosmetic science, food sciences, and health and life sciences.

Preface to the Second edition

Preface to the First edition

Chapter 1: Introduction

1.1 Role of chemistry in modern life

1.2 Solutions and concentrations

1.3 Suspension, colloid and emulsion

1.4 Electrolytes, nonelectrolytes and zwitterions

1.5 Osmosis and tonicity

1.6 Physical properties of drug molecules

1.6.1 Physical state

1.6.2 Melting point and boiling point

1.6.3 Polarity and solubility

1.7 Acid-base properties and pH

1.7.1 Acid-base definitions

1.7.2 Electronegativity and acidity 

1.7.3 Acid-base properties of organic functional groups

1.7.4 pH, pOH and pKa values

1.7.5 Acid-base titration: neutralisation

1.8 Buffer and its use

1.8.1 Common ion effects and buffer capacity

Chapter 2: Atomic Structure and Bonding

2.1 Atoms, elements and compounds

2.2 Atomic structure: orbitals and electronic configurations 

2.3 Chemical bonding theories: formation of chemical bonds

2.3.1 Lewis structures 

2.3.2 Resonance and resonance structures

2.3.3 Electronegativity and chemical bonding

2.3.4 Various types of chemical bonding

2.3.4.1 Ionic bonds

2.3.4.2 Covalent bonds

2.4 Bond polarity and intermolecular forces

2.4.1 Dipole-dipole interactions

2.4.2 van der Walls forces 

2.4.3 Hydrogen bonding

2.5 Hydrophilicity and lipophilicity 

2.6 Significance of chemical bonding in drug-receptor interactions

2.7 Significance of chemical bonding in protein-protein interactions

2.8 Significance of chemical bonding in protein-DNA interactions

Chapter 3: Stereochemistry

3.1 Stereochemistry: definition

3.2 Isomerism

3.2.1 Constitutional isomers

3.2.2 Stereoisomers

3.2.2.1 Conformational isomers

3.2.2.2 Configurational isomers 

3.3 Stereoisomerism of molecules with more than one stereocentres

3.3.1 Cyclic compounds

3.3.2 Geometrical isomers of alkenes and cyclic compounds

3.4 Significance of stereoisomerism in determining drug action and toxicity

3.5 Synthesis of chiral molecules

3.5.1 Racemic forms

3.5.2 Enantioselective synthesis

3.6 Separation of stereoisomers: resolution of racemic mixtures

3.7 Compounds with stereocentres other than carbon

3.8 Chiral compounds that do not have four different groups

Chapter 4: Organic Functional Groups

4.1 Organic functional groups: definition and structural features

4.2 Hydrocarbons 

4.3 Alkanes, cycloalkanes and their derivatives

4.3.1 Alkanes

4.3.2 Cycloalkanes

4.3.3 Alkyl halides

4.3.4 Alcohols

4.3.5 Ethers

4.3.6 Thiols

4.3.7 Thioethers

4.3.8 Amines

4.4 Carbonyl compounds

4.4.1 Aldehydes and ketones

4.4.2 Carboxylic acids 

4.4.3 Acid chlorides 

4.4.4 Acid anhydrides

4.4.5 Esters 

4.4.6 Amides 

4.4.7 Nitriles

4.5 Alkenes and their derivatives

4.5.1 Nomenclature of alkenes

4.5.2 Physical properties of alkenes

4.5.3 Structure of alkenes

4.5.4 Industrial uses of alkenes

4.5.5 Preparations of alkenes 

4.5.6 Reactivity and stability of alkenes

4.5.7 Reactions of alkenes 

4.6 Alkynes and their derivatives 

4.6.1 Nomenclature of alkynes

4.6.2 Structure of alkynes

4.6.3 Acidity of terminal alkynes

4.6.4 Heavy metal acetylides: test for terminal alkynes

4.6.5 Industrial uses of alkynes

4.6.6 Preparations of alkynes

4.6.7 Reactions of alkynes

4.6.8 Reactions of acetylides and alkynides

4.7 Aromatic compounds and their derivatives

4.7.1 History

4.7.2 Definition: Hückel’s rule

4.7.3 General properties of aromatic compounds

4.7.4 Classification of aromatic compounds

4.7.5 Pharmaceutical importance of aromatic compounds: some examples

4.7.6 Structure of benzene: Kekulé structure of benzene

4.7.7 Nomenclature of benzene derivatives

4.7.8 Electrophilic substitution of benzene

4.7.9 Alkylbenzene: toluene

4.7.10 Phenols

4.7.11 Aromatic amines: aniline

4.7.12 Polycyclic benzenoids

4.8 Importance of functional groups in determining drug actions and toxicity 

4.8.1 Structure-activity-relationships of sulpha drugs 

4.8.2 Structure activity relationships of penicillins 

4.8.3 Paracetamol toxicity

4.9 Importance of functional groups in determining stability of drugs

Chapter 5: Organic Reactions

5.1 Types of organic reactions occur with functional groups

5.2 Reaction mechanism and types of arrows in chemical reactions

5.3 Free radical reactions: chain reactions

5.3.1 Free radical chain reaction of alkanes

5.3.2 Relative stabilities of carbocations, carbanions, radicals and carbenes 

5.3.3 Allylic bromination

5.3.4 Radical inhibitors

5.4 Addition reactions

5.4.1 Electrophilic additions to alkenes and alkynes

5.4.2 Symmetrical and unsymmetrical addition to alkenes and alkynes

5.4.3 Nucleophilic addition to aldehydes and ketones

5.5 Elimination reactions: 1,2-elimination or β-elimination

5.5.1 E1 reaction or first order elimination

5.5.2 E2 reaction or second order elimination

5.5.3 Dehydration of alcohols

5.5.4 Dehydration of diols: pinacol rearrangement 

5.5.5 Base-catalysed dehydrohalogenation of alkyl halides

5.6 Substitution reactions

5.6.1 Nucleophilic substitutions

5.6.2 Nucleophilic substitutions of alkyl halides

5.6.3 Nucleophilic substitutions of alcohols

5.6.4 Nucleophilic substitutions of ethers and epoxides

5.6.5 Nucleophilic acyl substitutions of carboxylic acid derivatives

5.6.6 Substitution vs Elimination

5.7 Electrophilic substitutions

5.7.1 Electrophilic substitution of benzene

5.8 Hydrolysis

5.8.1 Hydrolysis of carboxylic acids derivatives

5.9 Oxidation-reduction reactions

5.9.1 Oxidising and reducing agents

5.9.2 Oxidation of alkenes 

5.9.3 Oxidation of alkynes 

5.9.4 Hydroxylation of alkenes

5.9.5 Oxidative cleavage of syn-diols 

5.9.6 Ozonolysis of alkenes

5.9.7 Ozonolysis of alkynes 

5.9.8 Oxidation of alcohols 

5.9.9 Oxidation of aldehydes and ketones 

5.9.10 Baeyer-Villiger oxidation of aldehydes or ketones

5.9.11 Reduction of alkyl halides

5.9.12 Reduction of organometallics 

5.9.13 Reduction of alcohols via tosylates 

5.9.14 Reduction of aldehydes and ketones

5.9.15 Clemmensen reduction 

5.9.16 Wolff-Kishner reduction

5.9.17 Reduction of acid chlorides 

5.9.18 Reduction of esters 

5.9.19 Hydride reduction of carboxylic acids

5.9.20 Reduction of oximes or imine derivatives 

5.9.21 Reduction of amides, azides and nitriles 

5.9.22 Reductive amination of aldehydes and ketones 

5.10 Pericyclic reactions

5.10.1 Diels-Alder reaction 

5.10.2 Essential structural features for dienes and dienophiles 

5.10.3 Stereochemistry of Diels-Alder reaction 

5.10.4 Sigmatropic rearrangements

5.10.5 Hydrogen shift

5.10.6 Alkyl shift: Cope rearrangement

5.10.7 Claisen rearrangement

Chapter 6: Heterocyclic compounds

6.1 Heterocyclic compounds and their derivatives

6.1.1 Medicinal importance of heterocyclic compounds 

6.1.2 Nomenclature of heterocyclic compounds

6.1.3 Physical properties of heterocyclic compounds 

6.2 Pyrrole, furan and thiophene: five-membered unsaturated heterocycles

6.2.1 Physical properties of pyrrole, furan and thiophene

6.2.2 Preparations of pyrrole, furan and thiophene

6.2.3 Reactions of pyrrole, furan and thiophene 

6.3 Pyridine 

6.3.1 Physical properties of pyridine 

6.3.2 Preparations of pyridine

6.3.3 Reactions of pyridine 

6.4 Oxazole, imidazole and thiazole

6.4.1 Physical properties of oxazole, imidazole and thiazole

6.4.2 Preparations of oxazole, imidazole and thiazole

6.4.3 Reactions of oxazole, imidazole and thiazole 

6.5 Isoxazole, pyrazole and isothiazole 

6.5.1 Physical properties of isoxazole, pyrazole and isothiazole 

6.5.2 Preparations of isoxazole, pyrazole and isothiazole 

6.5.3 Reactions of isoxazole, pyrazole and isothiazole

6.6 Pyrimidine

6.6.1 Physical properties of pyrimidine

6.6.2 Preparations of pyrimidine

6.6.3 Reactions of pyrimidine

6.7 Purine 

6.7.1 Physical properties of purine 

6.7.2 Preparations of purine

6.7.3 Reactions of purine

6.8 Quinoline and isoquinoline 

6.8.1 Physical properties of quinoline and isoquinoline

6.8.2 Preparations of quinoline and isoquinoline

6.8.3 Reactions of quinoline and isoquinoline 

6.9 Indole 

6.9.1 Physical properties of indole

6.9.2 Preparations of indole 

6.9.3 Reactions of indole 

6.9.4 Test for indole

Chapter 7: Nucleic acids

7.1 Nucleic acids

7.1.1 Synthesis of nucleosides and nucleotides 

7.1.2 Structure of nucleic acids 

7.1.3 Nucleic acids and heredity 

7.1.4 DNA fingerprinting

7.2 Amino acids and peptides 

7.2.1 Fundamental structural features of amino acid

7.2.2 Essential amino acids 

7.2.3 Glucogenic and ketogenic amino acids

7.2.4 Amino acids in human body 

7.2.5 Acid-base properties of amino acids 

7.2.6 Isoelectric points of amino acids and peptides

Chapter 8: Natural products chemistry

8.1 Introduction to natural products 

8.1.1 Natural products

8.1.2 Natural products in medicine

8.1.3 Drug discovery and natural products 

8.2 Alkaloids

8.2.1 Properties of alkaloids

8.2.2 Classification of alkaloids

8.2.3 Tests for alkaloids

8.3 Carbohydrates

8.3.1 Classification of carbohydrates

8.3.2 Stereochemistry of sugars

8.3.3 Cyclic structures of monosaccharides

8.3.4 Acetal and ketal formation in sugars

8.3.5 Oxidation, reduction, esterification and etherification of monosaccharides

8.3.6 Pharmaceutical uses of monosaccharides

8.3.7 Disaccharides

8.3.8 Polysaccharides

8.3.9 Miscellaneous carbohydrates

8.3.10 Cell surface carbohydrates and blood groupings

8.4 Glycosides

8.4.1 Biosynthesis of glycosides

8.4.2 Classification

8.4.3 Test for hydrocyanic acid (HCN)

8.4.4 Pharmaceutical uses and toxicity

8.4.5 Anthracene/anthraquinone glycosides

8.4.6 Isoprenoid glycosides

8.4.7 Iridoid and secoiridoid glycosides

8.5 Terpenoids

8.5.1 Classification

8.5.2 Biosynthesis of terpenoids

8.5.3 Monoterpenes

8.5.4 Sesquiterpenes

8.5.5 Diterpenes

8.5.6 Triterpenes

8.5.7 Tetraterpenes

8.6 Steroids

8.6.1 Structures of steroids

8.6.2 Stereochemistry of steroids

8.6.3 Physical properties of steroids

8.6.4 Types of steroids 

8.6.5 Biosynthesis of steroids

8.6.6 Synthetic steroids

8.6.7 Functions of steroids

8.7 Phenolics

8.7.1 Phenylpropanoids

8.7.2 Coumarins

8.7.3 Flavonoids and isoflavonoids

8.7.2 Lignans

8.7.5 Tannins

Index