Steering the antitumor drug discovery campaign towards structurally diverse indolines

Thakur, Amandeep; Singh, Arshdeep; Kaur, Navdeep; Ojha, Ritu; Nepali, Kunal

doi:10.1016/j.bioorg.2019.103436

Cited by 36 publications

(27 citation statements)

References 119 publications

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“…As a pivotal structure unit, hexahydrocarbazole motif widely occurs in many biologically active polycyclic indoline natural products 22 – 26 , such as kopsinine, tubifolidine, aspidospermidine, and vindoline (Fig. 1A ).…”

Section: Introductionmentioning

confidence: 99%

Stereoselective intermolecular radical cascade reactions of tryptophans or ɤ-alkenyl-α-amino acids with acrylamides via photoredox catalysis

Luo

Wang

et al. 2022

Nat Commun

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The radical cascade reaction is considered as one of the most powerful methods to build molecular complexity. However, highly stereoselective intermolecular radical cascade reactions that can produce complex cyclic compounds bearing multiple stereocenters via visible-light-induced photocatalysis have been challenging yet desirable. Herein we report a facile and efficient synthesis of multi-substituted trans-fused hexahydrocarbazoles via a stereoselective intermolecular radical cascade reaction of readily available tryptophans and acrylamides enabled by visible-light-induced photoredox catalysis. The trans-fused hexahydrocarbazoles with up to five stereocenters including two quaternary ones can be accessed in up to 82% yield, >20/1 diastereoselectivity, and 96% ee. Interestingly, the tetrahydrocarbazoles are favorably formed when the reaction is performed under air. Moreover, by simply switching the starting material from tryptophans to ɤ-alkenyl substituted α-amino acids, this protocol can be further applied to the stereoselective syntheses of 1,3,5-trisubstituted cyclohexanes which are otherwise challenging to access. Preliminary mechanistic studies suggest that the reaction goes through radical addition cascade and radical-polar crossover processes.

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Section: Introductionmentioning

confidence: 99%

Stereoselective intermolecular radical cascade reactions of tryptophans or ɤ-alkenyl-α-amino acids with acrylamides via photoredox catalysis

Luo

Wang

et al. 2022

Nat Commun

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“…Indoline scaffolds and spirocompounds are among the most widespread bioactive compounds, including anticancer agents; these compounds display diverse biological activities, such as inhibition of histone deacetylase and tubulin polymerization (Scheme 1). 2…”

Section: Introductionmentioning

confidence: 99%

The eco-friendly electrosynthesis of trifluoromethylated spirocyclic indolines and their anticancer activity

Lan

Lin

et al. 2022

Org. Biomol. Chem.

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“…The conditions screening presented in Table indicated that the selective formation of indolines 5 can be achieved, using the same Pd-catalyst with adducts 3 , by simple variation of the reaction conditions. The indoline core stands as one of the most ubiquitous heterocyclic components of pharmaceutical ingredients, agrochemicals, and naturally occurring molecules, and several methods for its stereoselective synthesis have been disclosed . However, the provision of stereodefined 3-vinyl-boronic ester analogues, such as 5 , is unprecedented.…”

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confidence: 99%

Modular Synthesis of Stereodefined Benzocyclobutene Derivatives via Sequential Cu- and Pd-Catalysis

et al. 2021

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Benzocyclobutenes (BCBs) are of growing interest in materials and medicinal chemistry, although general routes for their provision remain underexplored. A modular, divergent, and stereoselective Cu- and Pd-catalyzed assembly/cyclization sequence allows the synthesis of densely functionalized BCBs, from readily accessible imine, allene, and diboron precursors. Preliminary results have identified enantioselective conditions for our protocol and highlighted, for example, its applicability to the synthesis of BCB-containing peptides. By simple variation of experimental conditions or substrate modification, our strategy was expanded to deliver indoline and quinoline derivatives, suitable for further manipulations.

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Steering the antitumor drug discovery campaign towards structurally diverse indolines

Cited by 36 publications

References 119 publications

Stereoselective intermolecular radical cascade reactions of tryptophans or ɤ-alkenyl-α-amino acids with acrylamides via photoredox catalysis

Stereoselective intermolecular radical cascade reactions of tryptophans or ɤ-alkenyl-α-amino acids with acrylamides via photoredox catalysis

The eco-friendly electrosynthesis of trifluoromethylated spirocyclic indolines and their anticancer activity

Modular Synthesis of Stereodefined Benzocyclobutene Derivatives via Sequential Cu- and Pd-Catalysis

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