Holdings Information
The organic chemistry of medicinal agents / Adam Renslo.
Bibliographic Record Display
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Title:The organic chemistry of medicinal agents / Adam Renslo.
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Author/Creator:Renslo, Adam, author.
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Published/Created:New York : McGraw-Hill Education, [2016]
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Holdings
Holdings Record Display
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Location:WOODWARD LIBRARY stacksWhere is this?
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Call Number: QV55 .R46 2016
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Number of Items:1
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Status:Available
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Location:WOODWARD LIBRARY stacksWhere is this?
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Library of Congress Subjects: Pharmaceutical chemistry.
Chemistry, Organic.
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Medical Subjects:Pharmaceutical Preparations--chemistry.
Organic Chemistry Processes.
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Description:xi, 210 pages ; 27 cm
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Summary:Organic Chemistry for Pharmacy is a textbook written specifically for the students taking the required Organic/Medical Pharmacy course. Using a building- block approach, the book delivers a basic, yet thorough discussion of the mode of action, therapeutic applications, and limitations of various pharmaceutical agents.
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Notes:Includes index.
Includes bibliographical references and index.
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ISBN:9780071794213 paperback alkaline paper
0071794212
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Contents:Machine generated contents note: 1. Nature of Bonding in Organic Molecules / Dmitry Koltun
Introduction
Nature of Covalent and Ionic Bonds
Box 1.1 Drawing organic molecules
Polarization of Covalent Bonds
Atomic Orbitals and Valence Bond Theory
Hybridization of Orbitals and Tetrahedral Carbon
Hybrid Orbitals of Oxygen and Nitrogen and Common Functional Groups
Box 1.2 Functional groups containing phosphorus or sulfur
Aromaticity
Heteroaromatic Ring Systems in Drug Structures
Summary
Exercises
2. Non-Covalent Interactions / Adam Renslo
Introduction
Enthalpic and Entropic Contributions to Ligand/Drug Binding
Strength of Non-Covalent Interactions
Desolvation and the Hydrophobic Effect
Ionic Interactions
Box 2.1 Ionic interactions in a proton channel from influenza virus
Hydrogen Bonds
C
H Bonds as Hydrogen Bond Donors
Aryl Rings as Hydrogen Bond Acceptors
Box 2.2 - hydrogen bond in glutathione S-transferase
Aryl-Aryl Interactions
Cation-π Interactions
Box 2.3 Hydrophobic and cation-π interactions in the binding of neurotransmitters and drugs
Halogen Bonds
Box 2.4 C
F bonds as hydrogen bond acceptors and in orthogonal interactions with carbonyl groups
Summary
Case Study
-Inhibitors of Factor Xa as Anticoagulants
Exercises
3. Stereochemistry / Adam Renslo
Introduction
Chirality and the Shape of Molecules
Stereoisomers
-Some Important Definitions
Box 3.1 Determining isomeric and stereochemical relationships between molecules
Avoiding Confusion
Stereoisomers of 1,3-Dimethylcydohexane
Chirality Centers
Assigning the Configuration of Chirality Centers
Box 3.2 Cahn
Ingold
Prelog rules in brief
Configurational Assignment and Stereochemical Relationships
Meso Compounds
Chirality Centers at Non-Carbon Atoms
Other Sources of Chirality and Stereoisomerism
Box 3.3 Atropisomerism
Summary
Case Study
-Racemic and Non-Racemic Drugs
Exercises
4. Conformations of Organic Molecules / Adam Renslo
Introduction
Newman Projections and Dihedral Angles
Conformations and Energies of Ethane
-Torsional Strain
Conformations and Energies of Larger Acyclic Molecules
-Steric Strain
Conformations of Small Rings
Box 4.1 three major types of strain in organic molecules
Conformations of Cyclohexane and Related Six-Membered Rings
Estimating the Conformational Preferences of Substituted Cyclohexanes
Box 4.2 Drawing chair conformations
Conformationally Constrained Ring Systems
Box 4.3 Conformational constraint in opiate analgesics
Summary
Case Study
-Neuraminidase Inhibitors and the Influenza Virus
Exercises
5. Acid-Base Chemistry of Organic Molecules / Susan Miller
Introduction
Three Theories of Acids and Bases
Self-Ionization of Water and the pH Scale
Avoiding Confusion
-Use of "Acid" and "Base" and Related Terms
Acid Dissociation Constant Ka and pKa as a Measure of Acid Strength
Electronegativity and Size of Atoms and Acid/Base Strength
Atom Hybridization and Acid/Base Strength
Resonance Electronic Effects on Acid/Base Strength
Inductive Electronic Effects of Substituents on Acid/Base Strength
Combined Inductive and Resonance Effects on Acid/Base Strength
Proximity and Through-Space Effects on Acid/Base Strength
Henderson-Hasselbalch Relationship and Acid/Base Equilibria as a Function of pH
Summary
Case Study
-Discovery of Tagamet
Exercises
6. Nucleophilic Substitution, Addition, and Elimination Reactions / Adam Renslo
Introduction
Nucleophiles
Electrophiles
Box 6.1 Electrophiles in cancer drugs
Leaving Groups
Nucleophilic Aliphatic Substitution Reactions
SN2
Box 6.2 SN2 reactions in biological chemistry
Nucleophilic Aliphatic Substitution Reactions
-SN1
Neighboring Group Assistance in SXI1 Reactions
Nucleophilic Aromatic Substitution
SNAr
Addition Reactions
Elimination Reactions
E1 and E2
Summary
Case Study
Drugs That Form a Covalent Bond to Their Target
Exercises
7. Reactions of Carbonyl Species / Adam Renslo
Introduction
Nature of the Carbonyl Group
Relative Reactivity of Carbonyl-Containing Functional Groups
Hydration of Aldehydes and Ketones
Reactions of Aldehydes and Ketones with Alcohols
Box 7.1 Glucuronidation in the metabolism of drugs
Imines and Enamines
Box 7.2 Imines in drug-protein conjugates
Oximes and Hydrazones
Chemical Hydrolysis of Ester and Amide Bonds
Enzymatic Hydrolysis of Peptide Bonds by Proteases
Box 7.3 Drugs designed to inhibit proteases
Summary
Case Study
-Odanacatib
Exercises
8. Radical Chemistry / Adam Renslo
Introduction
Formation, Stability, and Molecular Orbital View of Radicals
Radical Reactions
Reactions of Molecular Oxygen
Iron-Mediated Radical Reactions in Drug Metabolism
Box 8.1 Fenton chemistry in the action of antimalarial drugs
Summary
Case Study
-Calicheamicin γ1
Exercises
Solutions to Exercises.