1st Edition

Isoquinoline Alkaloids



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ISBN 9789057022296
Published June 2, 1998 by CRC Press
512 Pages

USD $425.00

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Book 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

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