Indolo[2,3-a]quinolizidines and Derivatives: Bioactivity and Asymmetric Synthesis

Pérez, Maria; Espadinha, Margarida; Santos, Maria M. M.

doi:10.2174/1381612821666151002112934

Cited by 12 publications

(3 citation statements)

References 37 publications

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“…The asymmetric synthesis of indoloquinolizidines was achieved starting from enantiopure tryptophanol, a methodology used previously by the groups of Allin [19,20] and Amat-Bosch [21,22,23,24,25,26,27] for the synthesis of several indole alkaloids. In this synthetic strategy, tryptophanol is used not only as the source of chirality, but is also used to incorporate the tryptamine moiety present in the target alkaloids [28,29].…”

Section: Resultsmentioning

confidence: 99%

Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists

et al. 2016

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Enantiopure tryptophanol is easily obtained from the reduction of its parent natural amino acid trypthophan (available from the chiral pool), and can be used as chiral auxiliary/inductor to control the stereochemical course of a diastereoselective reaction. Furthermore, enantiopure tryptophanol is useful for the syntheses of natural products or biological active molecules containing the aminoalcohol functionality. In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity as N-Methyl D-Aspartate (NMDA) receptor antagonists. The indolo[2,3-a]quinolizidine scaffold was obtained using the following key steps: (i) a stereoselective cyclocondensation of (S)-or (R)-tryptophanol with appropriate racemic δ-oxoesters; (ii) a stereocontrolled cyclization on the indole nucleus. The synthesized enantiopure indolo[2,3-a]quinolizidines were evaluated as NMDA receptor antagonists and one compound was identified to be 2.9-fold more potent as NMDA receptor blocker than amantadine (used in the clinic for Parkinson's disease). This compound represents a hit compound for the development of novel NMDA receptor antagonists with potential applications in neurodegenerative disorders associated with overactivation of NMDA receptors.

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Section: Resultsmentioning

confidence: 99%

Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists

et al. 2016

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“…The indoloquinolizine moiety is a usual framework that is found in biologically significant naturally occurring compounds and pharmaceuticals for example arborescidine A 290 and nauclefidine 291 . Thus, the establishment of unique methods to obtain these framework has been obtained much attention [139] . Brominated alkaloids of tetrahydro‐β‐carboline group were extracted from the marine tunicate pseudodistoma arborescens and identified as arborescidine A 290 [140] .…”

Section: Application Of Stetter Reaction In Total Synthesis Of Naturamentioning

confidence: 99%

“…Thus, the establishment of unique methods to obtain these framework has been obtained much attention. [139] Brominated alkaloids of tetrahydro-β-carboline group were extracted from the marine tunicate pseudodistoma arborescens and identified as arborescidine A 290. [140] Nauclefidine, extracted from nauclea officinals, has been utilized as an antibacterial and anti-inflammatory agent as folk medicine in China.…”

Section: Hirota and Co-workers In 2003 Isolated Tetrapetalones Frommentioning

confidence: 99%

Recent Advances in Stetter Reaction and Related Chemistry: An update

et al. 2020

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The Stetter reaction is actually a special CÀ C bond forming reaction through a 1,4-addition reaction in the presence of nucleophilic catalyst. It involves a reaction between aldehydes and Michael acceptors catalyzed by Nheterocyclic carbenes (NHC's) leading to preparation of 1,4dicarbonyl compounds via carbon-carbon bond formation. It offers a powerful approach to access 1,4-dicarbonyl compounds which are significant starting materials and inter-mediates in the synthesis of several heterocyclic systems, and bioactive heterocyclic framework which are present in natural products. In this review we try to underscore the recent advances in Stetter reaction and its applications from 2015 till date. Notably, we focused on the applications of Stetter reaction in the synthesis of various heterocyclic systems and total synthesis of natural products, which have largely been overlooked, previously.

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Recent Advances in N‐Heterocyclic Carbene Catalyzed Oxidative Cyclization for the Formation of Heterocycles

2021

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Oxidative N‐heterocyclic carbene catalyst mediated cyclization proved to be an efficient strategy for the construction of various N‐ and O‐ heterocycles. Among several metal‐free methods available for the construction of heterocyclic compounds, oxidative NHC catalysis proved to be an elegant and efficient strategy as several enantioenriched compounds with excellent enantioselectivities can be synthesized in good yields. The most common method of the generation of these heterocycles proceeds via the commonly encountered intermediate in oxidative NHC catalysis (i. e.) acyl azolium intermediate. This intermediate proves to be the active species as it can undergo reaction with suitable substrates leading to the formation of numerous N‐ and O‐ heterocycles. Herein, recent reports on different strategies that enable formal [2+2], [3+2], [3+3], [4+2] or [4+3] annulations between the incoming substrates and acyl azolium species or other active intermediates which can add to suitable substrate leading to various heterocycles were summarized.

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Indolo[2,3-a]quinolizidines and Derivatives: Bioactivity and Asymmetric Synthesis

Cited by 12 publications

References 37 publications

Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists

Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists

Recent Advances in Stetter Reaction and Related Chemistry: An update

Recent Advances in N‐Heterocyclic Carbene Catalyzed Oxidative Cyclization for the Formation of Heterocycles

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