Synthesis of .BETA.- and .GAMMA.-Carbolines and Their N-Oxides from 2(or 3)-Ethynylindole-3(or 2)-carbaldehydes.

Sakamoto, Takao; Numata, Atsushi; Saitoh, Hironori; Kondo, Yoshinori

doi:10.1248/cpb.47.1740

Cited by 19 publications

(6 citation statements)

References 6 publications

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“…Similar types of syntheses of g-carbolines involving carbonyls of aldehydes [159 -163], ketones [93,94,118,162], carboxylic acids [164], and esters [163] were reported. Groups such as -CH(CN)Me, -CH(CN)Et, -CH(CN)CHNMe 2 [158], -CH(COOEt)NH 2 [161], -CH 2 COOMe [160,163], -CH(COOMe) 2 [160,162], -CºC-Ph [153], -CºC-But [153,159], -CH 2 CN [93,94,158,165], -CH 2 CONHMe, -CH 2 CONHBn [164], and others in the indole 2-position were used.…”

Section: Scheme 34mentioning

confidence: 99%

“…Here, acetylindoxyl (159) was first reacted with p-nitrophenylaniline in a two-step synthesis to afford 3-p-nitrophenylaminoindole (160), which underwent a Vilsmeier reaction that resulted in the formation of 2-formyl-3-p-nitrophenylaminoindole (161). Reaction of 161 with malondinitrile occurred smoothly to give the corresponding 2-dicyanovinylindole (162), heating of which in the presence of potash in acetone cleaved the C=C bond and formed aldehyde 161 as the main product.…”

Section: Scheme 53mentioning

confidence: 99%

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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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Section: Scheme 34mentioning

confidence: 99%

Section: Scheme 53mentioning

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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“…γ‐Carbolines can be synthesized by various strategies, such as the Graebe–Ullmann procedure, Pictet–Spengler cyclization, Fischer or alkyne Pd‐ or Pd/Cu‐catalyzed annulations, ring‐closing metathesis, or tandem Suzuki–Miyaura/S N Ar or intramolecular Diels–Alder reactions . Another interesting synthetic pathway, reported by Sakamoto, employs the formation of monosubstituted N ‐oxide B (Scheme ) from the corresponding oxime A under basic conditions . However, none of these approaches can simultaneously generate the tricyclic core and provide the correct positioning of various C2 and C4 substituents in a one‐pot procedure.…”

Section: Introductionmentioning

confidence: 99%

“…[10] Another interesting synthetic pathway, reported by Sakamoto, employs the formation of monosubstituted N-oxide B (Scheme 1) from the corresponding oxime A under basic conditions. [11] However, none of these approaches can simultaneously generate the tricyclic core and provide the correct positioning of various C2 and C4 substituents in a one-pot procedure. This paper reports an original strategy for construction of the γ-carboline pyridine ring with simultaneous functionalization of the γ-carboline C2 and C4 positions.…”

Section: Introductionmentioning

confidence: 99%

Tandem Silver‐Catalyzed Cyclization/Nucleophilic Functionalization of 2‐Alkynylindole‐3‐carbaldehyde Oximes to Afford New 2,4‐Disubstituted γ‐Carbolines

et al. 2016

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Highly substituted pyrido[4,3‐b]indole derivatives were synthesized through a straightforward one‐pot silver‐catalyzed process involving 2‐alkynylindole‐3‐carbaldehyde oximes. The tandem cyclization/nucleophilic addition sequence was optimized and applied to a wide range of nucleophiles, which reacted regioselectively at the pyrido[4,3‐b]indole C4 position. The scope and limitations of the methodology were evaluated and the final compounds were obtained in fair to very good yields. This versatile method proved to be compatible with various chemical functionalities or (hetero)cycles.

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“…∆ + A similar synthesis scheme was put forward by Japanese authors [53] without reference to the previous work of Russian scientists [52], and they used the method to produce the N-oxides of both γ-and β-carbolines. The products from the condensation of the 2-ethynyl-3-formylindoles themselves with ammonia were γ-carbolines [53]. .…”

mentioning

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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Synthesis of .BETA.- and .GAMMA.-Carbolines and Their N-Oxides from 2(or 3)-Ethynylindole-3(or 2)-carbaldehydes.

Cited by 19 publications

References 6 publications

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

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

Tandem Silver‐Catalyzed Cyclization/Nucleophilic Functionalization of 2‐Alkynylindole‐3‐carbaldehyde Oximes to Afford New 2,4‐Disubstituted γ‐Carbolines

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

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