TEXT-BOOK OF ORGANIC CHEMISTRY FOR MEDICAL STUDENTS

By BARBARA JOHNSON

CONTENTS 1 INTRODUCTION ROLE OF CHEMISTRY IN MODERN LIFE PHYSICAL PROPERTIES OF DRUG MOLECULES 2 ATOMIC STRUCTURE AND BONDING ATOMS, ELEMENTS AND COMPOUNDS ATOMIC STRUCTURE: ORBITALS AND ELECTRONIC CON?GURATIONS CHEMICAL BONDING THEORIES: FORMATION OF CHEMICAL BONDS ELECTRONEGATIVITY AND CHEMICAL BONDING BOND POLARITY AND INTERMOLECULAR FORCES SIGNI?CANCE OF CHEMICAL BONDING IN DRUG–RECEPTOR INTERACTIONS 3 STEREOCHEMISTRY STEREOCHEMISTRY: DE?NITION ISOMERISM SIGNI?CANCE OF STEREOISOMERISM IN DETERMINING DRUG ACTION AND TOXICITY SYNTHESIS OF CHIRAL MOLECULES SEPARATION OF STEREOISOMERS: RESOLUTION OF RACEMIC MIXTURES COMPOUNDS WITH STEREOCENTRES OTHER THAN CARBON CHIRAL COMPOUNDS THAT DO NOT HAVE A TETRAHEDRAL ATOM WITH FOUR DIFFERENT GROUPS 4 ORGANIC FUNCTIONAL GROUPS ORGANIC FUNCTIONAL GROUPS: DE?NITION AND STRUCTURAL FEATURES HYDROCARBONS ALKANES, CYCLOALKANES AND THEIR DERIVATIVES ALKENES AND THEIR DERIVATIVES ALKYNES AND THEIR DERIVATIVES AROMATIC COMPOUNDS AND THEIR DERIVATIVES HETEROCYCLIC COMPOUNDS AND THEIR DERIVATIVES NUCLEIC ACIDS AMINO ACIDS AND PEPTIDES 4 10 IMPORTANCE OF FUNCTIONAL GROUPS IN DETERMINING DRUG ACTIONS AND TOXICITY 4 11 IMPORTANCE OF FUNCTIONAL GROUPS IN DETERMINING STABILITY OF DRUGS 5 ORGANIC REACTIONS TYPES OF ORGANIC REACTION RADICAL REACTIONS: FREE RADICAL CHAIN REACTIONS ADDITION REACTIONS ELIMINATION REACTIONS: 1,2-ELIMINATION OR B-ELIMINATION 5 5 SUBSTITUTION REACTIONS 5 6 HYDROLYSIS 5 7 OXIDATION–REDUCTION REACTIONS 5 8 PERICYCLIC REACTIONS 6 NATURAL PRODUCT CHEMISTRY 6 1 INTRODUCTION TO NATURAL PRODUCT DRUG DISCOVERY PROCESS 6 2 ALKALOIDS 6 3 CARBOHYDRATES 6 4 GLYCOSIDES 6 5 TERPENOIDS 6 6 STEROIDS 6 7 PHENOLICS