InterBioScreen Monograph Series

SELECTED METHODS
FOR SYNTHESIS AND MODIFICATION
OF HETEROCYCLES

CARBOLINE: CHEMISTRY AND BIOLOGICAL ACTIVITY

Edited by Prof. V.G. Kartsev

International Editorial Board:

Prof. Bergman J. (Sweden)
Prof. Corey E.J. (USA, Nobel Prize in Chemistry 1990)
Prof. Huisgen R. (Germany)
Prof. Katritzky A.R. (USA)
Prof. Lehn J.-M. (France, Nobel Prize in Chemistry 1987)
Prof. Nemes A. (Hungary)
Prof. Noyori R. (Japan, Nobel Prize in Chemistry 2001)
Prof. Van der Plas H.C. (Netherlands)

5 Volume, 624 pages,
Moscow: Published by the International Charitable Foundation Scientific Partnership (ICSPF), 2006


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SELECTED METHODS
FOR SYNTHESIS AND MODIFICATION
OF HETEROCYCLES

CARBOLINES:
CHEMISTRY AND BIOLOGICAL
ACTIVITY


Edited by Prof. V.G. Kartsev




Volume 5




ICSPF
Moscow - 2006

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Dedicated to my Teachers: Prof. A.N. Kost and
Academician N.M. Emanuel

Prof. Viktor G. Kartsev
President, International Foundation Scientific Partnership Chairman,
Board of directors of InterBioScreen Ltd.

 

This book, vol. 5 of the monograph series Selected Methods for Synthesis and Modification of Heterocycles, is devoted to the chemistry and biological activity of carbolines, the largest group of known alkaloids. Most carboline systems are produced by plants (e.g. of the Apocynaceae, Loganiaceae, Rubiaceae, etc. families), some fungi, microorganisms, marine invertebrates and mammals. More than 95% of natural carbolines and carboline-containing drugs are derivatives of b-carbolines, although other isomeric systems-a-, g-, and d-carbolines-are also known as bioactive alkaloids.

The exceptionally important property of the majority of naturally occuring and synthethic carbolines is their high and diverse biological activity. For instance, well known is the anti-inflammatory and anti-arrhythmic activity of the alkaloid Ajmaline 1 that is capable of cutting short the attack of ciliary arrhythmia and paroxysmal tachycardia. The synthetic drug Incazane 2, a reversible inhibitor of Type A , activates the noradrenergic and serotonergic processes in CNS and retards the reverse neuronal capture of monoamines.

The semi-synthetic analog of the alkaloid vincamine, drug Cavinton 3, dilates brain blood vessels, intensifies blood flow, and suppresses the aggregation of thrombocytes. Its structural analog, Vindeburnol 4, exhibits the cardiotinic and cerebroprotective activity.

The a-carboline alkaloid Isogranulatimide 5 from the ascidia Didemnum granulatum acts as the G2-specific inhibitor of cell cycle. The synthetic g-carboline drug Diazoline 6, an effective blocker of H1 receptors, is being widely used for treating pollinosis, nettle-rash, neurodermatitis, hay fever, etc.

Rarely encountered d- and a-carboline alkaloids-such as Norcryptolepine 7 and Quinindoline 8-are known to act as stong antibacterial, antiherpetic, antimalarial, and antihyperglycemic agents.

This volume contains detailed reviews of the chemistry and biological activity of the above four types of carboline systems, both naturally occurring and synthetic.

As the previous books of the series, this volume is also supplemented with the most interesting protocols for the synthesis and modification of heterocycles developed by chemists from different countries all over the world. Some of these protocols have been elaborated under the inspiration and support from InterBioScreen. The book is published in Russian and English simultaneously.

The series Selected Methods for Synthesis and Modification of Heterocycles is published on the initiative and with support of InterBioScreen and the International Foundation Scientific Partnership.

I sincerely believe that this monograph will be interesting and useful to scientists who work in the field of chemistry and biological activity of synthetic and naturally occurring heterocycles.

 


CONTENTS
VOLUME 5

Granik V.G.
The chemistry of d-carbolines

7

Nemes A.
Eburnamine/vincamine alkaloids

43
Shults E.E., Tolstikov G.A., Kartsev V.G.
Naturally occurring a-, g-, d-carbolines and their analogs: Synthesis and biological activity

77
Shults E.E., Tolstikov G.A., Kartsev V.G.
Natural b-carbolines: Synthesis and biological activity
153
Tolkunov S.V., Kibal'nyi .V., Dulenko V.I.
b-Carbolines: Synthesis and chemical behavior
300
Tolkunov S.V., Popov V.Yu.
5-Pyrido[4,3-b]indoles (g-carbolines)
349
Tuskaev V..
Synthesis of b-carbolines
393
 
Selected methods for synthesis and modification of carbolines
423-616
 

Author index
617-621

 


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