Cephalosporins and Penicillins

Chemistry and Biology

1st Edition - January 1, 1972
Editor: Edwin H. Flynn
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 2 - 7 0 1 7 - 3

Cephalosporins and Penicillins: Chemistry and Biology describes the studies made on cephalosporin in relation to the scientific and medicinal benefits that can be derived from… Read more

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Cephalosporins and Penicillins: Chemistry and Biology describes the studies made on cephalosporin in relation to the scientific and medicinal benefits that can be derived from cephalosporin C. This collection discusses how cephalosporin C is produced through modern isolation methods. One paper discusses its structure through chemical means, its degradation products, its derivative and other metabolic products such as penicillin N and cephalosporin P. Another paper explains the preparation method for 7-aminocephalosporanic acid and 6-aminopenicillanic acid through biological or chemical means. Another paper explains the alteration of the dihydrothiazine ring of the cephalosporins as the functionalities of these rings are chemically difficult to obtain. One paper also explains the rearrangements of cephalosporins and penicillins; cephalosporin can be synthesized from penicillin through an intermediacy of penicillin sulfoxide. Other papers discuss the pharmacology and toxicology of cephalosporins, as well as the practical tests and methods of assay that can be used in most cephalosporins, and in some cases, in penicillins. This book can prove useful for pharmacologists, microchemists, research workers, and technologists dealing with toxicology.

List of Contributors

Preface

Chapter 1 Cephalosporin Coder

I. Occurrence of the Cephalosporins

II. History of Development

III. Chemical Determination of Structure

IV. Degradation Products of Cephalosporin C

V. Derivatives of Cephalosporin C

VI. Other Metabolic Products of Cephalosporium sp.

References

Chapter 2 Preparative Methods for 7-Aminocephalosporanic Acid and 6-Aminopenicillanic Acid

General Remarks

I. Biological Methods

II. Chemical Methods

References

Chapter 3 Modifications of the ß-Lactam System

I. Reactions of the Side Chain Amino Group

II. Modifications at the ß-Lactam Carbons

III. Cleavage of the ß-Lactam

References

Chapter 4 Alteration of the Dihydrothiazine Ring Moiety

I. Introduction

II. Reactions at Sulfur (S-1)

III. Modifications at C-2

IV. Reactions of the Cephem Double Bond

V. Modifications at C-3

VI. Modifications of the C-4 Carboxyl Group

References

Chapter 5 Rearrangements of Cephalosporins and Penicillins

I. Introduction

II. Synthesis of Cephalosporin from Penicillin via Intermediacy of Penicillin Sulfoxide

III. Synthesis of Cephalosporin from Penicillin via an Azetidinone-Thiazolidine

IV. Attempted Synthesis of Cephalosporin from Penicillanyl Alcohol

V. Attempted Synthesis of Cephalosporin from Anhydropenicillin

VI. Some Miscellaneous Reactions of ß-Lactam Compounds

References

Chapter 6 Total Syntheses of Penicillins and Cephalosporins

I. Introduction

II. The Total Synthesis of Penicillin

III. The Total Synthesis of Cephalosporins

IV. Modified ß-Lactam Antibiotics

References

Chapter 7 Chemical and Biological Activity: Inferences from X-Ray Crystal Structures

I. Introduction

II. Crystallographic Results

III. Structure-Activity Relationships

IV. Summary

References

Chapter 8 Physical-Chemical Properties of Cephalosporins and Penicillins

I. Introduction

II. Dissociation Constants

III. Infrared Spectroscopy

IV. Mass Spectroscopy

V. Nuclear Magnetic Resonance

VI. Ultraviolet Spectroscopy

References

Chapter 9 Microbial Synthesis of Cephalosporin and Penicillin Compounds

I. Introduction

II. Tripeptide Theory

III. Biosynthesis of ß-Lactam Antibiotics and Primary Metabolism

IV. The Biology of Pénicillium and Cephalosporium

V. Modification of ß-Lactam Antibiotics by Enzymes from Pénicillium and Cephalosporium

VI. Conclusions

References

Chapter 10 Biological Reactions of Cephalosporins and Penicillins

I. The Action of j8-Lactamases on Penicillins and Cephalosporins

II. Mode of Action of Penicillins and Cephalosporins Against Bacteria

III. Serum Binding of Penicillins and Cephalosporins

IV. Allergy to Penicillins and Cephalosporins

References

Chapter 11 Biological Evaluation

I. Introduction

II. Methodology

III. Biological Properties of Cephalosporin Antibiotics from a Laboratory Standpoint

IV. Resistance to Cephalosporins by Staphylococci

V. Disc-Susceptibility Testing

References

Chapter 12 Structure-Activity Relationships of ß-Lactam Antibiotics

I. Introduction

II. Sources of Antibiotics

III. Scope to this Review

IV. Factors Affecting Antibacterial Activity

V. Evaluation

VI. Test Methods

VII. Comparison of Penicillins and Cephalosporins

VIII. Cephalosporins Substituted at C-3

IX. Cephalosporins Substituted at C-2

X. Cephalosporins Substituted at C-7

XI. Miscellaneous Compounds with Diminished Activity

XII. Conclusions

References

Chapter 13 Pharmacology and Toxicology of Cephalosporins

I. Introduction

II. Toxicology of Cephalosporins in Therapeutic Use

III. Absorption, Distribution, and Excretion of Cephalosporins in Therapeutic Use

IV. Metabolism of Cephalosporins in Therapeutic Use

V. Pharmacology of Cefazolin

References

Chapter 14 Analytical Procedures for Cephalosporins

I. Introduction

II. Microbiological Determinations

III. Chemical Determinations

IV. Chromatographie Determinations

V. Physical-Chemical Determinations

References

Chapter 15 ß-Lactam Antibiotics from Streptomyces

I. Introduction

II. Characteristic of the ß-Lactam-Producing Cultures

III. Production and Isolation of ß-Lactam Antibiotics from Streptomyces

IV. Physical-Chemical Properties

V. Determination of Structure

VI. Conversion of Cephalosporin C to 7-(5-amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

VII. Circular Dichroism Studies

VIII. Biosynthetic Studies

References

Chapter 16 Appendix

I. Preparative Procedures

References

II. Analytical Methods

III. Physical-Chemical Data

References

Author Index

Subject Index