Isoquinoline Alkaloids: 1st Edition (Hardback) book cover

Isoquinoline Alkaloids

1st Edition

By K. W. Bentley

CRC Press

512 pages

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Hardback: 9789057022296
pub: 1998-06-02
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Description

The Isoquinoline Alkaloids presents an in-depth review of 22-sub groups of isoquinoline alkaloids all related to their common origin from the amino-acids phenylalanine and tyrosine. The coverage is not intended to be comprehensive and encyclopaedic, but all of the salient features of the elucidation of structures, structural variation, stereochemistry, chemical reactions, syntheses, biogenetic origins and relationships, and pharmacology are covered, and an extensive bibliography of original papers is provided to assist further detailed study.

The opening chapter comprises a review of the formation of alkaloids from amino-acids and the general methods of structural degradation used in the definitive elucidations of structures. Two final chapters cover napthylisoquinolines, which are biogenetically distinct from those discussed in earlier chapters, and miscellaneous natural products that are rationally included with other groups.

This book should be of interest to graduates and researchers in the field of organic chemistry, natural product chemistry and biochemistry.

Table of Contents

1. ISOQUINOLINE ALKALOIDS - ORIGINS AND DEGREDATION

2. ß-PHENYLETHYLAMINES AND SIMPLE ISOQUINOLINES

2.1 Structures

2.2 Syntheses

2.3 Chemical Properties

2.4 Polymeric Isoquinolines

2.5 N-Benzylisoquinolines

2.6 1-Phenylisoquinolines

2.7 4-Phenylisoquinolines

2.8 Biogenesis

2.9 Pharmacology

References

3. 1-BENZOISOQUINOLINES

3.1 Structures

3.2 Syntheses

3.3 Chemical Properties

3.4 Biogenesis

3.5 Pharmacology

References

4. BISBENZYLISOQUINOLINES

4.1 Singly-Linked Dimers

4.2 Doubly-Linked Dimers

4.3 Triply-Linked Dimers

4.4 Oxidised Alkaloids

4.5 Benzoisoquinoline-Benzodiazepine Dimer

4.6 Syntheses

4.7 Biogenesis

4.8 Pharmacology

References

5. CULARINE AND RELATED ALKALOIDS

5.1 Structures

5.2 Oxidised Alkaloids

5.3 A Rearranged Alkaloid

5.4 Cularine-Morphinan Dimers

5.5 Syntheses

5.6 Biogenesis

5.7 Pharmacology

References

6. PAVINES AND ISOPAVINES

6.1 Pavine Alkaloids

6.2 Isopavine Alkaloids

6.3 Syntheses

6.4 Dimeric Alkaloids

6.5 Biogenesis

6.6 Pharmacology

References

7. DIBENZOPYRROCOLINES

7.1 Structures

7.2 Biogenesis

References

8. APORPHINOID ALKALOIDS

8.1 Aporphines

8.2 Syntheses of Aporphines

8.3 Secoaporphines

8.4 Oxoaporphines

8.5 Dioxoaporphines

8.6 Aristolactams

8.7 Aristolochic Acids

8.8 Dimeric Aporphines

8.9 Proaporphines

8.10 Aporphinoid-Benzylisoquinoline Dimers

8.11 Oxo-isoaporphines

8.12 Azafluoranthenes and Related Tropolones

8.13 Ring-C Cleaved Alkaloids

8.14 Biogenesis of Aporphinoid Alkaloids

8.15 Pharmacology

References

9. EMETINE AND RELATED ALKALOIDS

9.1 Benzylisoquinoline Dimers

9.2 Benzylisoquinoline-Tryptamine Dimers

9.3 Monobasic Alkaloids

9.4 Azaberberines

9.5 Syntheses

9.6 Biogenesis

9.7 Pharmacology

References

10. BERBERINES AND TETRAHYDROBERBERINES

10.1 Determination of Structure

10.2 General Reactions of Berberine

10.3 Reactions of Tetrahydroberberines

10.4 Syntheses

10.5 Bimolecular Berberines

10.6 Biogenesis

10.7 Pharmacology

References

11. SECOBERBERINES

11.1 Structures

11.2 Syntheses

11.3 Biogenesis

11.4 Pharmacology

References

12. PHTHALIDE-ISOQUINOLINES

12.1 Structures

12.2 Modified Alkaloids

12.3 Syntheses

12.4 Biogenesis

12.5 Pharmacology

References

13. PROTOPINES

13.1 Structures

13.2 Syntheses

13.3 Biogenesis

13.4 Pharmacology

References

14. SPIRO-BENZYLISOQUINOLINES

14.1 Structures

14.2 Syntheses

14.3 Biogenesis

14.4 Pharmacology

References

15. INDANOBENZAEPINES

15.1 2,3-Indano-4,5-benzaepines

15.2 6,7-Indano-3,4-benzaepines

15.3 Pharmacology

References

16. RHOEADINES

16.1 Structures

16.2 Syntheses

16.3 Biogenesis

16.4 Pharmacology

References

17. BENZOPHENANTHRIDINES

17.1 Structures

17.2 Syntheses

17.3 Biogenesis

17.4 Pharmacology

References

18. OTHER MODIFIED BERBERINES

18.1 Isoindolobenzazepines

18.2 Isoindoloiosquinolines

18.3 Isoindolobenzazepines

18.4 Spirobenzazepines

18.5 Isoquinolinoisoquinolines

18.6 Biogenesis

References

19. PHENETHYLISOQUINOLINES

19.1 Phenethylisoquinolines

19.2 Bisphenethylisoquinolines

19.3 Homoaporphines

19.4 Homoproaporphines

19.5 Homoaporphinan Alkaloids

19.6 Syntheses

19.7 Biogenesis

19.8 Azaproaporphines

References

20. COLCHICINE AND RELATED ALKALOIDS

20.1 Colchicine

20.2 Analogues of Colchicine

20.3 Reactions of Colchicine

20.4 Ring-contracted Alkaloids

20.5 Syntheses

20.6 Biogenesis

20.7 Pharmacology

References

21. ERYTHRINA ALKALOIDS

21.1 Structures

21.2 Alkaloids of Cocculus Species

21.3 Azaerythrinanes

21.4 Syntheses

21.5 Biogenesis

21.6 Pharmacology

References

22. HOMOERYTHRINA ALKALOIDS

22.1 Structures

22.2 Syntheses

22.3 Biogenesis

22.4 Pharmacology

References

23. CEPHALOTAXINE AND RELATED ALKALOIDS

23.1 Structures

23.2 Syntheses

23.3 Biogenesis

23.4 Pharmacology

References

24. NAPTHYLIOSQUINOLINES

24.1 Structures

24.2 Syntheses

24.3 Biogenesis

24.4 Pharmacology

References

25. OTHER ISOQUINOLINE ALKALOIDS

25.1 Jamtine N-oxide

25.2 Leptocarpine

25.3 Aaptamine

25.4 Necatorone

25.5 Mimosamycin

25.6 Mimocin

25.7 Renierone

25.8 Saframycins A, B and C

25.9 Naphthyridinomycin

25.10 Quinocarcin (quinocarmycin)

25.11 Ecteinascidins

References

26. ADDENDA

Index

Subject Categories

BISAC Subject Codes/Headings:
SCI011000
SCIENCE / Life Sciences / Botany
SCI013000
SCIENCE / Chemistry / General
SCI013040
SCIENCE / Chemistry / Organic