Indole derivatives as tubulin polymerization inhibitors for the development of promising anticancer agents

Hong, Yu Jin; Zhu, Yuan‐Yuan; He, Qiuqin; Gu, Shuang‐Xi

doi:10.1016/j.bmc.2021.116597

Cited by 27 publications

(21 citation statements)

References 129 publications

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“…[54,55] The N-1, C-2 to C-6, or C-7 positions of indole can be substituted to produce versatile indole derivatives, demonstrating a diverse scaffold for drug design. [56][57][58][59] Recently, a new strategy for the photocatalytic production of Friedel-Crafts alkylation at C-3 position of indoles the reaction of indoles and nitroalkenes has been reported, where water has been used as a green solvent. [60] However, relatively high temperature (60 °C) was required to accelerate these reactions.…”

Section: Methodsmentioning

confidence: 99%

pH‐Triggered Recovery of Organic Polymer Photocatalytic Particles for the Production of High Value Compounds and Enhanced Recyclability

Heuer

Kuckhoff

et al. 2023

Angew Chem Int Ed

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Pseudo-homogeneous polymeric photocatalysts are an emerging class of highly efficient and tunable photocatalytic materials, where the photocatalytic centers are easily accessible. The creation of highly efficient photocatalytic materials that can be rapidly separated and recovered is one of the critical challenges in photocatalytic chemistry. Here, we describe pHresponsive photocatalytic nanoparticles that are active and well-dispersed under acidic conditions but aggregate instantly upon elevation of pH, enabling easy recovery. These responsive photocatalytic polymers can be used in various photocatalytic transformations, including Cr VI reduction and photoredox alkylation of indole derivative. Notably, the cationic nature of the photocatalyst accelerates reaction rate of an anionic substrate compared to uncharged species. These photocatalytic particles could be readily recycled allowing multiple successive photocatalytic reactions with no clear loss in activity.

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Section: Methodsmentioning

confidence: 99%

pH‐Triggered Recovery of Organic Polymer Photocatalytic Particles for the Production of High Value Compounds and Enhanced Recyclability

Heuer

Kuckhoff

et al. 2023

Angew Chem Int Ed

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“…Meanwhile, the yields of the products decreased in the order of para -substituent, meta -substituent, and ortho -substituent, probably due to the steric hindrance ( 7ba , 7la , and 7ia ). Considering the importance of heterocyclic compounds in medicinal chemistry, the furan [ 38 , 39 ], thiophene [ 40 , 41 , 42 , 43 ], and indole [ 44 , 45 , 46 , 47 ] moieties were all installed to the arenes, and the desired products 7na-7qa were furnished in 36–93% yields. On the other hand, the tolerance of vinylogous malononitrile derivative 3 were also investigated.…”

Section: Resultsmentioning

confidence: 99%

DBU Promoted Polysubstituted Arene Formation via a Michael Addition/Cyclization/Elimination Cascade Reaction

et al. 2022

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The straightforward construction of polysubstituted arenes is essential in both synthetic chemistry and medicinal chemistry. Herein, we reported a DBU promoted Michael addition/cyclization/elimination cascade reaction between vinylogous malononitrile derivatives and chlorinated nitrostyrenes for the synthesis of polysubstituted arenes. The method features mild reaction conditions, wide substrate scope and high yield. Interestingly, preliminary study of the enantioselective version of this cascade was conducted to give chiral biaryl atropisomers with up to 40% ee through center-to-axial chirality transfer strategy.

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“…[54,55] Die N-1-, C-2-bis C-6-oder C-7-Positionen von Indol können substituiert werden, um vielseitige Indolderivate herzustellen, die ein vielfältiges Gerüst für die Entwicklung von Arzneimitteln darstellen. [56][57][58][59] Kürzlich wurde über eine neue Strategie für die photokatalytische Herstellung von Friedel-Crafts-Alkylierung an der C-3-Position von Indolen durch die Reaktion von Indolen und Nitroalkenen berichtet, wobei Wasser als grünes Lösungsmittel verwendet wurde. [60] Allerdings war eine relativ hohe Temperatur ( 60 Indolderivaten unter Blaulichtbestrahlung ohne Photokatalysator bei Raumtemperatur stattfand.…”

Section: Das Aufkommen Von Mit Sichtbarem Licht Anregbarenunclassified

pH‐getriggerte Rückgewinnung von photokatalytischen Partikeln aus organischen Polymeren zur Herstellung hochwertiger Verbindungen und verbesserter Recyclingfähigkeit

Heuer

Kuckhoff

et al. 2023

Angewandte Chemie

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Pseudohomogene polymere Photokatalysatoren sind eine neue Klasse hocheffizienter und einstellbarer photokatalytischer Materialien, bei denen die photokatalytischen Zentren leicht zugänglich sind. Die Schaffung hocheffizienter photokatalytischer Materialien, die schnell abgetrennt und zurückgewonnen werden können, ist eine der entscheidenden Herausforderungen in der photokatalytischen Chemie. Hier beschreiben wir auf den pH‐Wert reagierende photokatalytische Nanopartikel, die unter sauren Bedingungen aktiv und gut dispergiert sind, aber bei Erhöhung des pH‐Werts sofort aggregieren und so eine einfache Rückgewinnung ermöglichen. Diese auf den pH‐Wert reagierenden photokatalytischen Polymere können für verschiedene photokatalytische Umwandlungen verwendet werden, darunter die Reduktion von CrVI und die Photoredoxalkylierung von Indolderivaten. Insbesondere beschleunigt die kationische Natur des Photokatalysators die Reaktionsgeschwindigkeit eines anionischen Substrats im Vergleich zu ungeladenen Spezies. Diese photokatalytischen Partikel können leicht recycelt werden und ermöglichen mehrere aufeinanderfolgende photokatalytische Reaktionen ohne deutlichen Aktivitätsverlust.

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Indole derivatives as tubulin polymerization inhibitors for the development of promising anticancer agents

Cited by 27 publications

References 129 publications

pH‐Triggered Recovery of Organic Polymer Photocatalytic Particles for the Production of High Value Compounds and Enhanced Recyclability

pH‐Triggered Recovery of Organic Polymer Photocatalytic Particles for the Production of High Value Compounds and Enhanced Recyclability

DBU Promoted Polysubstituted Arene Formation via a Michael Addition/Cyclization/Elimination Cascade Reaction

pH‐getriggerte Rückgewinnung von photokatalytischen Partikeln aus organischen Polymeren zur Herstellung hochwertiger Verbindungen und verbesserter Recyclingfähigkeit

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