Bioorganic and Medicinal Chemistry of Fluorine / Edition 1

Hardcover (Print)
Buy New
Buy New from BN.com
$141.78
Used and New from Other Sellers
Used and New from Other Sellers
from $30.69
Usually ships in 1-2 business days
(Save 79%)
Other sellers (Hardcover)
  • All (7) from $30.69   
  • New (5) from $114.23   
  • Used (2) from $30.69   
Close
Sort by
Page 1 of 1
Showing All
Note: Marketplace items are not eligible for any BN.com coupons and promotions
$30.69
Seller since 2009

Feedback rating:

(9)

Condition:

New — never opened or used in original packaging.

Like New — packaging may have been opened. A "Like New" item is suitable to give as a gift.

Very Good — may have minor signs of wear on packaging but item works perfectly and has no damage.

Good — item is in good condition but packaging may have signs of shelf wear/aging or torn packaging. All specific defects should be noted in the Comments section associated with each item.

Acceptable — item is in working order but may show signs of wear such as scratches or torn packaging. All specific defects should be noted in the Comments section associated with each item.

Used — An item that has been opened and may show signs of wear. All specific defects should be noted in the Comments section associated with each item.

Refurbished — A used item that has been renewed or updated and verified to be in proper working condition. Not necessarily completed by the original manufacturer.

Very Good
New York 2008 Hardcover No Card Pocket Near Fine Ex-Library Condition 8vo-over 7?-9?" tall Covers the influence of fluorine on the structural properties of a molecule and on a ... molecule's biological behavior, using examples of fluorinated drugs to provide a thorough overview of the role of fluorine in pharmaceutical science and development. Yellow/grey glossy boards. Minimal library markings; clean and tightly bound. Read more Show Less

Ships from: Hopeland, PA

Usually ships in 1-2 business days

  • Canadian
  • International
  • Standard, 48 States
  • Standard (AK, HI)
  • Express, 48 States
  • Express (AK, HI)
$114.23
Seller since 2008

Feedback rating:

(4686)

Condition: New
New Book. Shipped from UK within 10 to 14 business days. Established seller since 2000.

Ships from: Horcott Rd, Fairford, United Kingdom

Usually ships in 1-2 business days

  • Standard, 48 States
  • Standard (AK, HI)
$114.24
Seller since 2008

Feedback rating:

(18484)

Condition: New
Brand New, Perfect Condition, Please allow 4-14 business days for delivery. 100% Money Back Guarantee, Over 1,000,000 customers served.

Ships from: Westminster, MD

Usually ships in 1-2 business days

  • Canadian
  • International
  • Standard, 48 States
  • Standard (AK, HI)
$118.89
Seller since 2009

Feedback rating:

(11187)

Condition: New
New Book. Shipped from US within 10 to 14 business days. Established seller since 2000.

Ships from: Secaucus, NJ

Usually ships in 1-2 business days

  • Standard, 48 States
  • Standard (AK, HI)
$119.76
Seller since 2007

Feedback rating:

(23914)

Condition: New
BRAND NEW

Ships from: Avenel, NJ

Usually ships in 1-2 business days

  • Canadian
  • International
  • Standard, 48 States
  • Standard (AK, HI)
$136.17
Seller since 2015

Feedback rating:

(0)

Condition: New
0470278307 Premium Publisher Direct Books are Like New or Brand New books direct from the publisher sometimes at a discount. Multiple copies are usually available. These books ... are not available for expedited shipping and may take up to 14 business days to receive. Read more Show Less

Ships from: Agoura Hills, CA

Usually ships in 1-2 business days

  • Standard, 48 States
  • Express, 48 States
$141.77
Seller since 2008

Feedback rating:

(18484)

Condition: Like New
Brand New, Perfect Condition, Please allow 4-14 business days for delivery. 100% Money Back Guarantee, Over 1,000,000 customers served.

Ships from: Westminster, MD

Usually ships in 1-2 business days

  • Canadian
  • International
  • Standard, 48 States
  • Standard (AK, HI)
Page 1 of 1
Showing All
Close
Sort by

Overview

  • Provides a thorough overview of the role of fluorine in pharmaceutical science and development
  • Includes chapters on fluorinated analogues of natural products, fluorinated amino acids and peptides, and derivatives of sugars
  • Classifies marketed and in-development fluorinated pharmaceuticals according to their therapeutic classes
Read More Show Less

Editorial Reviews

From the Publisher
"This is an excellent book for those contemplating incorporation of fluorine into their drug design research investigations and how it can be accomplished. It is also an excellent reference book for experts in the area. I enthusiastically recommend adding this to both individual and library collections." (Journal of Medicinal Chemistry, December 25, 2008)

"The book is clearly written and has been adequately translated … .Its compact size, and abundance of helpful schemes, figures, tables and structures make it convenient aid for the practicing scientist." (Journal of the American Chemical Society, December 31, 2008)

"I am pleased to recommend Bioorganic and Medicinal Chemistry of Fluorine as an invaluable reference source and stimulus to further research, for pharmaceutical and medicinal chemists, organic chemists, and biochemists in academia and industry, and for advanced students and instructors in these fields." (Angewandte Chemie, October 13, 2008)

Read More Show Less

Product Details

  • ISBN-13: 9780470278307
  • Publisher: Wiley
  • Publication date: 5/27/2008
  • Edition number: 1
  • Pages: 366
  • Product dimensions: 6.20 (w) x 9.30 (h) x 1.00 (d)

Meet the Author

Jean-Pierre Begue, PHD, is Emeritus Director of Research at the Centre National de la recherche Scientifique (CNRS) in France. Danièle Bonnet-Delpon, PHD, is Director of Research at CNRS. The authors and their coworkers have developed the chemistry of fluorinated compounds, from organic synthesis to medicinal chemistry.

Read More Show Less

Table of Contents

Foreword.

Preface to the English Edition

1 General Remarks on Structural, Physical, and Chemical Properties of Fluorinated Compounds.

1.1 Structural Effects.

1.2 Physical Properties.

1.2.1 Boiling Point.

1.2.2 Surface Tension and Activity.

1.2.3 Polarity-Solubility.

1.2.4 Lipophilicity.

1.3 Effects on Electronic Properties and Reactivity.

1.3.1 Effects of Fluorination on Bond Energies and Reactivity.

1.3.2 Effects of Fluorination on the Electronic Repartition of a Molecule.

1.3.3 Acidity, Basicity, and Hydrogen Bond.

1.3.4 Steric Effects.

1.3.5 Fluorination Effects on the Stability of Reaction Intermediates (Carbocations, Carbanions, and Radicals).

References.

2 Overview on the Preparation of Fluorinated Compounds.

2.1 Preparation of Monofluorinated Compounds.

2.1.1 Nucleophilic Fluorination.

2.1.2 Electrophilic Fluorination.

2.1.3 Formation of Carbon–Carbon Bonds Starting from Monofluorinated Synthons.

2.2 Preparation of Difluorinated Compounds.

2.2.1 Nucleophilic Fluorination.

2.2.2 Electrophilic Fluorination.

2.2.3 Starting from Di- and Trifluoromethyl Compounds.

2.3 Preparation of Trifluoromethyl Compounds.

2.3.1 Fluorination.

2.3.2 Nucleophilic Trifluoromethylation.

2.3.3 Electrophilic Trifluoromethylation.

2.3.4 Radical Trifluoromethylation.

2.3.5 Metal-Catalyzed Trifluoromethylation.

2.3.6 Formation of Carbon–Carbon Bonds from Trifluoromethyl Compounds.

2.4 Synthesis of Perfluoroalkyl Compounds.

References.

3 Effects of Fluorine Substitution on Biological Properties.

3.1 Affinity for the Macromolecule Target.

3.1.1 Steric Effects.

3.1.2 Conformational Changes.

3.1.3 Dipolar Interactions and Electric Field.

3.1.4 Hydrogen Bonds and Other Weak Interactions.

3.1.5 pKa of Amines.

3.1.6 Fluorous Interactions.

3.2 Absorption.

3.2.1 Lipophilicity.

3.2.2 pKa and Solubility.

3.3 Metabolism.

3.3.1 Oxidative Metabolism.

3.3.2 Hydrolytic Metabolism.

3.4 Modification of Chemical Reactivity: Enzyme Inhibitors.

3.4.1 Analogue of Substrates as Inhibitors.

3.4.2 Inhibition by Stabilization or Destabilization of Intermediates of Biological Processes.

3.4.3 Irreversible Inhibition with Mechanism-Based Inhibitors (Suicide Substrates).

References.

4 Fluorinated Analogues of Natural Products.

4.1 Fluorinated Products in Nature.

4.2 Steroids.

4.2.1 Corticosteroids.

4.2.2 Steroids with Trifluoromethyl Groups in Angular Position.

4.2.3 Fluorinated Analogues of Metabolites of Vitamin D3.

4.2.4 Other Fluorinated Steroids.

4.3 Terpenes.

4.3.1 Artemisinin.

4.3.2 Taxol.

4.4 Pigments and Vitamins.

4.4.1 Retinoids.

4.4.2 Carotenoids.

4.4.3 Vitamin D.

4.4.4 Vitamins E and K.

4.4.5 Porphyrins.

4.5 Lipids and Prostanoids.

4.6 Pheromones and Toxins.

4.7 Alkaloids.

4.7.1 Vinca Alkaloids.

4.7.2 Cinchona Alkaloids.

4.7.3 Camptothecin.

4.7.4 Other Fluorinated Alkaloids.

4.8 Macrolides.

4.8.1 Epothilone.

4.8.2 Erythromycin.

4.8.3 Amphotericin B.

4.8.4 Avermectin.

4.9 Anthracyclines.

References.

5 Fluorinated Derivatives of a-Amino Acids and Proteins.

5.1 Fluorinated Aliphatic Amino Acids.

5.1.1 Alanines.

5.1.2 Valines, Leucines, and Isoleucines.

5.1.3 Prolines.

5.2 Aromatic Amino Acids: Phenylalanine, Tyrosine, Histidine, and Tryptophan.

5.3 Functional Fluorinated Amino Acids.

5.3.1 Serines and Threonines.

5.3.2 Aspartic Acids and Arginines.

5.3.3 Glutamic Acids and Glutamines.

5.3.4 Lysine, Ornithine, and Arginine.

5.3.5 Cysteines and Methionines.

5.4 -Fluoroalkyl Amino Acids.

5.4.1 Mono- and Difluoromethyl Amino Acids.

5.4.2 -Trifluoromethyl Amino Acids.

5.5 Incorporation of Fluorinated Amino Acids into Peptides and Proteins.

5.5.1 Polypeptides.

5.5.2 Proteins.

References.

6 Saccharidic Fluorinated Derivatives.

6.1 Glycosyl Fluorides.

6.2 Mono- and Difluorinated Analogues of Sugars.

6.2.1 Fluorinated Furanoses and Nucleosides.

6.2.2 Fluorinated Pyranoses.

6.3 Fluoromethyl Derivatives of Sugars.

6.3.1 Difluorovinyl Compounds.

6.3.2 Difluoromethylene-C-Glycosides.

6.3.3 C-Difluoromethyl Glycosides.

6.3.4 Trifluoromethylated Sugars.

6.4 Perfluoroalkylated Sugars.

6.4.1 Preparation of C-Perfluoroalkyl Sugars.

6.4.2 O- and S-Fluoroalkyl Glycosides.

6.4.3 Applications of Amphiphilic Fluoroalkyl Sugars.

References.

7 Inhibition of Enzymes by Fluorinated Compounds.

7.1 Substrate Analogues.

7.1.1 Fluorine Replaces a Hydrogen Involved in the Catalytic Cycle.

7.1.2 Fluorine Replaces a Hydroxyl.

7.1.3 Fluorinated Analogues of Substrates in Which Fluorine is Not Directly Involved in the Inhibition..

7.2 Destabilization of Reaction Intermediates (or of Transition States) of Enzymatic Processes by Fluorinated Groups.

7.2.1 Prenyl Transfer.

7.2.2 Inhibition of Glycosidases and Glycosyltransferases.

7.2.3 Inhibition of UDP-GlcNAC Enolpyruvyltransferase (MurZ).

7.2.4 Enolpyruvate Shikimate Phosphate Synthase (EPSPS).

7.3 Inhibitors that are Analogues of the Transition State: Di- and Trifluoromethyl Ketones.

7.3.1 Serine Enzymes.

7.3.2 Inhibition of Aspartyl Enzymes.

7.3.3 Inhibition of Metalloproteases.

7.3.4 Cysteine Protease and Thiol Enzymes.

7.4 Mechanism-Based Inhibitors.

7.4.1 Inhibition of Pyridoxal Phosphate Enzymes.

7.4.2 Thymidylate Synthase.

7.4.3 Inhibition of Monoamine Oxidases.

7.4.4 D-Ala-D-Ala Dipeptidase (VanX).

7.4.5 Inhibition of Ribonucleotide Diphosphate Reductase.

7.4.6 Inhibition of S-Adenosylhomocysteine Hydrolase.

7.4.7 Inhibition of Cytidine-50-diphosphate-D-Glucose.

4,6-Dehydratase (CDP D-Glucose 4,6-Dehydratase).

7.4.8 Other Irreversible Inhibitors.

7.5 Fluorinated Inhibitors Involving a Still Unknown Mechanism.

7.5.1 Inhibition of the Steroid C17(20)lyase.

7.5.2 Phosphatidylinositol Phospholipase C (PI-PLC).

7.5.3 Inhibition of the Protein of Transfer of Cholesteryl Esters.

7.5.4 -Fluoropolyamines as Inhibitors of the Biosynthesis of Polyamines.

7.5.5 Inhibition of the Biosynthesis of Cholesterol.

References.

8 Fluorinated Drugs.

8.1 Antitumor and Antiviral Fluorinated Drugs.

8.1.1 Fluoronucleosides.

8.1.2 Other Antitumor and Antiviral Drugs.

8.2 Anti-infectious Drugs.

8.2.1 Fluorinated Antibiotic Drugs.

8.2.2 Antifungal Drugs.

8.2.3 Fluorinated Drugs for Parasitic Diseases.

8.3 Drugs for CNS Disorders.

8.3.1 Neuroleptics.

8.3.2 Drugs for Depressive Disorders.

8.3.3 Anxiolytics and Sedatives.

8.3.4 Other Drugs for CNS Disorders.

8.4 Drugs of Inflammatory and Immunity Disorders.

8.4.1 Fluorocorticosteroids.

8.4.2 H1 Antagonist Antiallergics.

8.4.3 Drugs for Asthma and Respiratory Disorders.

8.4.4 Analgesic and Antiarthritic Drugs.

8.5 Drugs for Cardiovascular Disorders.

8.5.1 Cholesterol Lowering Drugs.

8.5.2 Drugs for Hypertension.

8.5.3 Drugs for Arrhythmias.

8.5.4 Antithrombosis and Anticoagulant Fluorinated Agents.

8.6 Drugs for Gastrointestinal Disorders.

8.6.1 Prevention and Treatment of Ulcer.

8.6.2 Antiemetic Agents.

8.6.3 Drugs for Bowel Disorders.

8.7 Drugs for Endocrine and Metabolic Disorders.

8.7.1 Drugs Acting on Steroid Hormone Receptors.

8.7.2 Drugs for Benign Prostatic Hypertrophy (BPH).

8.7.3 Drugs for Other Urologic Disorders.

8.7.4 Drugs for Calcemia Disorders.

8.7.5 Drugs for Diabetes.

8.7.6 Drugs for Hepatic Disorders.

8.8 Miscellaneous.

8.8.1 Drugs for Ophthalmic Disorders.

8.8.2 Drugs for Genetic Disease.

8.8.3 Contrast and Diagnostic Agents.

8.9 Highly Fluorinated Compounds with Clinical Uses.

8.9.1 General Anesthetics.

8.9.2 Therapeutic Uses of Perfluorocarbons.

8.10 Fluorinated Functions and Motifs in Medicinal Chemistry.

8.10.1 Fluorinated Ethers.

8.10.2 Fluorinated Alcohols and Amines.

8.10.3 Fluorinated Ketones.

8.10.4 Fluoroalkyl Groups.

Appendix: INN and Trademark Names.

References.

Index.

Read More Show Less

Customer Reviews

Be the first to write a review
( 0 )
Rating Distribution

5 Star

(0)

4 Star

(0)

3 Star

(0)

2 Star

(0)

1 Star

(0)

Your Rating:

Your Name: Create a Pen Name or

Barnes & Noble.com Review Rules

Our reader reviews allow you to share your comments on titles you liked, or didn't, with others. By submitting an online review, you are representing to Barnes & Noble.com that all information contained in your review is original and accurate in all respects, and that the submission of such content by you and the posting of such content by Barnes & Noble.com does not and will not violate the rights of any third party. Please follow the rules below to help ensure that your review can be posted.

Reviews by Our Customers Under the Age of 13

We highly value and respect everyone's opinion concerning the titles we offer. However, we cannot allow persons under the age of 13 to have accounts at BN.com or to post customer reviews. Please see our Terms of Use for more details.

What to exclude from your review:

Please do not write about reviews, commentary, or information posted on the product page. If you see any errors in the information on the product page, please send us an email.

Reviews should not contain any of the following:

  • - HTML tags, profanity, obscenities, vulgarities, or comments that defame anyone
  • - Time-sensitive information such as tour dates, signings, lectures, etc.
  • - Single-word reviews. Other people will read your review to discover why you liked or didn't like the title. Be descriptive.
  • - Comments focusing on the author or that may ruin the ending for others
  • - Phone numbers, addresses, URLs
  • - Pricing and availability information or alternative ordering information
  • - Advertisements or commercial solicitation

Reminder:

  • - By submitting a review, you grant to Barnes & Noble.com and its sublicensees the royalty-free, perpetual, irrevocable right and license to use the review in accordance with the Barnes & Noble.com Terms of Use.
  • - Barnes & Noble.com reserves the right not to post any review -- particularly those that do not follow the terms and conditions of these Rules. Barnes & Noble.com also reserves the right to remove any review at any time without notice.
  • - See Terms of Use for other conditions and disclaimers.
Search for Products You'd Like to Recommend

Recommend other products that relate to your review. Just search for them below and share!

Create a Pen Name

Your Pen Name is your unique identity on BN.com. It will appear on the reviews you write and other website activities. Your Pen Name cannot be edited, changed or deleted once submitted.

 
Your Pen Name can be any combination of alphanumeric characters (plus - and _), and must be at least two characters long.

Continue Anonymously

    If you find inappropriate content, please report it to Barnes & Noble
    Why is this product inappropriate?
    Comments (optional)