Synthesis of pyrazino[1,2-a]indoles and indolo-[1,2-a]quinoxalines (microreview)

Соколова, Е. А.; Festa, Alexey А.

doi:10.1007/s10593-016-1866-y

Cited by 13 publications

(6 citation statements)

References 20 publications

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“…The broad abundance of indoles in biological systems made this heterocycle a privileged scaffold for medicinal and pharmaceutical chemistry, agrochemicals, and materials. , The development of novel methods for the preparation and functionalization of indoles has been in the focus of researchers for decades . The synthesis of annulated indoles attracts much attention too, e.g., pyrazino[1,2- a ]indoles are sought for heterocycles with a diverse array of biological activities . Some representative examples, most relevant to current research, display antiproliferative activity, bind to DNA, and inhibit CK2, PIM1, and PIM2 , (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Divergent Transformations of N-(Propargyl)indole-2-carbonitriles with Nitrogen Nucleophiles: Alkyne Hydroamination or Domino Cyclizations

et al. 2022

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Interactions of N-(propargyl)indole-2-carbonitrileswith nitrogen nucleophiles were studied. It was found that lithium hexamethyldisilazane (LiHMDS)-promoted reactions give mixtures of two product types, originating from an initial attack onto carbon−carbon or carbon−nitrogen triple bonds. Performing the reaction at reduced temperature and in the presence of catalytic amounts of LiHMDS delivered alkyne hydroamination products exclusively. On the contrary, the one-pot reaction of N-(propargyl)indole-2-carbonitriles with methanol and LiHMDS on heating, followed by the addition of a nitrogen nucleophile, allowed a selective domino cyclization sequence toward 1-aminopyrazino-[1,2-a]indoles. Anilines and nitrogen heterocycles could be employed as N-nucleophiles to obtain products of both types. Moreover, an alternative one-pot route toward a third product type has been developed. When N-(propargyl)indole-2-carbonitrile was first combined with aniline and LiHMDS at reduced temperature, further heating of the in situ generated hydroamination product led to the intramolecular cyclization into 1-imino-2-phenylpyrazino[1,2-a]indoles. Thus, chemodivergent transformations of the same starting material into three compound classes were investigated. The possible reaction routes were studied, and N-(allenyl)indole-2carbonitrile was identified as the key intermediate. Acyclic and cyclic products exhibit fluorescence emission in the blue to green range.

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Section: Introductionmentioning

confidence: 99%

Chemoselective Divergent Transformations of N-(Propargyl)indole-2-carbonitriles with Nitrogen Nucleophiles: Alkyne Hydroamination or Domino Cyclizations

et al. 2022

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“…The access to this substituted aromatic nucleus has been well studied since 1997 by the chemist community from a synthetic point of view and for its potential in medicinal chemistry [ 1 , 2 ]. In parallel, structural modifications of the pyrazino[1,2- a ]indole nucleus showed that (3,4-dihydro)pyrazino[1,2- a ]indoles (type A) and (3,4-dihydro)-pyrazino[1,2- a ]indol-1-ones (type B) were efficient pharmacophores used in a variety of diseases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activities of Pyrazino[1,2-a]indole and Pyrazino[1,2-a]indol-1-one Derivatives

et al. 2021

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This review concerns the synthesis and biological activities of pyrazino[1,2-a]indoles and pyrazino[1,2-a]indol-1-ones reported since 1997 and the discovery of biological activity of pyrazinoindole derivatives. In the first part, we first presented the synthetic routes that have been reported from a methodological point of view to access the pyrazinoindole unit according to cyclization reactions using or not using metal catalysts. Then, syntheses and neuropsychiatric, auto-immune, anti-infectious and anti-cancer properties of pyrazinoindoles were detailed. In the second part, we first reported the main accesses to pyrazinoindol-1-one substrates according to Michael reactions, metal-catalyzed and metal-free cyclization reactions. The syntheses and anti-cancer, anti-infectious, anti-allergenic and neuropsychiatric properties of pyrazinoindolones were next described and discussed.

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“…Finally, the third way is the binding of bio‐active compounds to DNA double helical structures. In a simple term, the efficiency of bio‐active compounds or drugs depends on the binding affinity of DNA molecular microenvironment …”

Section: Introductionmentioning

confidence: 99%

“…In a simple term, the efficiency of bio-active compounds or drugs depends on the binding affinity of DNA molecular microenvironment. [5] Calf thymus DNA (ctDNA) is widely used as a model DNA to investigate the binding interaction mechanism between biologically active compounds and DNA molecules. [8][9][10][11][12]44] The objective of this work is to find the binding domain of pyrazino [1,2-a] indole compound with ctDNA to understand more about this compound efficiency in the biological environment.…”

Section: Introductionmentioning

confidence: 99%

Understanding the Binding Mechanism of a Pyrazino[1,2‐a]indole Derivative with Calf Thymus DNA

et al. 2019

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This work was focused on understanding the interaction mechanism of pyrazino[1,2‐a]indole derivative in calf thymus DNA (ctDNA) using various spectroscopy and computational techniques. The UV‐Vis absorption result shows that the binding interaction of pyrazino[1,2‐a]indole derivative in ctDNA complex may be in the non –covalent form and the binding associate constant Ka value was estimated 7.06×103 L mol−1 at 297 K. The fluorescence emission spectroscopy analysis suggested that pyrazino[1,2‐a]indole derivative quenching mechanism in ctDNA mainly due to the static nature and thermodynamical parameter analysis implied the binding of pyrazino[1,2‐a]indole derivative in ctDNA mainly due to hydrophobic force. Forster resonance energy transfer analysis was also calculated and the r=2.1 nm. Circular dichroism spectra conclude that there is a change in the secondary structural region of ctDNA due to an interaction with pyrazino[1,2‐a]indole derivative. Together with the molecular docking studies, hydrophobic nature of the interaction of pyrazino[1,2‐a]indole derivative with ctDNA might be deduced.

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Synthesis of pyrazino[1,2-a]indoles and indolo-[1,2-a]quinoxalines (microreview)

Cited by 13 publications

References 20 publications

Chemoselective Divergent Transformations of N-(Propargyl)indole-2-carbonitriles with Nitrogen Nucleophiles: Alkyne Hydroamination or Domino Cyclizations

Chemoselective Divergent Transformations of N-(Propargyl)indole-2-carbonitriles with Nitrogen Nucleophiles: Alkyne Hydroamination or Domino Cyclizations

Synthesis and Biological Activities of Pyrazino[1,2-a]indole and Pyrazino[1,2-a]indol-1-one Derivatives

Understanding the Binding Mechanism of a Pyrazino[1,2‐a]indole Derivative with Calf Thymus DNA

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