Acetals of lactams and acid amides. 60. Novel approach to the synthesis of ?-carbolines

Krichevskii, E. S.; Алексеева, Л. М.; Граник, В. Г.

doi:10.1007/bf00476976

Cited by 2 publications

(2 citation statements)

References 5 publications

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“…The dienaminocarbonyl structural fragment is a convenient five-carbon component for the construction of the pyridine ring by reaction with ammonia or primary amines. The use of the dienaminocarbonyl fragment, often contained in a substituted indole ring, leads to γ-carboline structures [40]. Depending on the temperature, Vilsmeier formylation of 2-cyanomethylindole leads to the formation of 2-(1-cyano-2-dimethylaminovinyl)-3-formyl-and 2-cyanomethyl-3-formyl-indoles, which in reaction with ammonia are converted into 4-cyano-and 3-amino-γ-carbolines respectively [38].…”

Section: Methods Of Synthesis Of γ-Carbolinesmentioning

confidence: 99%

γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review)

Alekseyev

Kurkin

Yurovskaya

2009

Chem Heterocycl Comp

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Section: Methods Of Synthesis Of γ-Carbolinesmentioning

confidence: 99%

γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review)

Alekseyev

Kurkin

Yurovskaya

2009

Chem Heterocycl Comp

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“…Transamination of 1-substituted 2-(b-dimethylaminovinyl)-5-nitro-3-formylindoles (127a-c) by saturated ammonia in MeOH was accompanied by cyclization to pyridine to give g-carbolines 128a-c (Scheme 41) [155].…”

Section: Scheme 34mentioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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The main trends in the development of the chemistry of a-, g-, and d-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe-Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.Four classes of pyridoindoles, i.e., carbolines (1 -4), are known. Of these, b-carbolines (2) have been studied most completely. Numerous studies, including several reviews [1 -3], have addressed the synthesis and various properties of this class of compounds. The properties of the other carbolines have been studied in less detail, e.g., their syntheses and chemical and physicochemical properties have not yet been discussed and compared in the literature.A detailed comparison seems especially important because precisely such an analysis can expose the basic features that make these classes chemically and biologically significant. This is especially important during research directed at the discovery of new biologically active compounds. Because the large volume of literature dedicated to b-carbolines makes it practically impossible to discuss it in a single review, the present review is limited to a comparison of the other carbolines only, the syntheses of which have been discussed much less in the literature. We intend to discuss the main trends in the development of the chemistry of a-, g-, and d-carbolines without pretending to include all literature in its entirety in order to compare the potential of finding novel effective drugs in these series. We discuss first reviews dedicated to pyridoindoles [2 -5], including a rather recent review of g-carbolines [6]. Then we switch to chemical approaches to the synthesis of selected carboline derivatives, noting briefly publications on their biological properties.Pyridoindoles (carbolines), including pyrido[4,3-b]indoles (g-carbolines), some of which exhibit a broad spectrum of biological activity, are definitely interesting. Drugs of this class already exist, e.g., neuroleptic carbidine 5 (Carbidinum or Stobadine) and dimebon antihistamine drugs 6 (Dimebonum) and diazoline 7 (Diazolinum or Omeril) [7,8]. Furthermore, dimebon exhibited pronounced anti-NMDA (N-methyl-D-asparate, ED 50 = 42 mg/kg i.p.) and anticalcium activity (blocks calcium channels, IC 50 = 57 mM) and inhibited acetylcholinesterase (ACE) and butyrylcholinesterase (BuCE) (IC 50 = 42 and 7.9 mM, respectively) in in vitro tests. It also had pronounced cognitive-stimulant properties in in vivo tests for a neurotoxic 654 0091-150X/11/4412-0654

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Acetals of lactams and acid amides. 60. Novel approach to the synthesis of ?-carbolines

Cited by 2 publications

References 5 publications

γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review)

γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review)

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

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