Intramolecular Diels–Alder reaction for the synthesis of tetracyclic carbazoles and isocanthines

Naik, Prajakta N.; Khan, Ayesha; Kusurkar, Radhika S.

doi:10.1016/j.tet.2013.10.054

Cited by 20 publications

(5 citation statements)

References 17 publications

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“…The cytotoxicity of three dihydro-4 H -pyrido[3,2,1 -jk ]carbazole derivatives was evaluated against HeLa cell lines. Carbazoles 38 , 39 and 40 (Figure 48) showed moderate activity with IC 50 values of 19.80, 17.46 and 18.76 µM, respectively 82 .…”

Section: Tetracyclic Fused Carbazolesmentioning

confidence: 99%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

117

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For over half a century, the carbazole skeleton has been the key structural motif of many biologically active compounds including natural and synthetic products. Carbazoles have taken an important part in all the existing anti-cancer drugs because of their discovery from a large variety of organisms, including bacteria, fungi, plants, and animals. In this article, we specifically explored the literature from 2012 to 2018 on the anti-tumour activities reported to carbazole derivatives and we have critically collected the most significant data. The most described carbazole anti-tumour agents were classified according to their structure, starting from the tricyclic–carbazole motif to fused tetra-, penta-, hexa- and heptacyclic carbazoles. To date, three derivatives are available on the market and approved in cancer therapy.

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Section: Tetracyclic Fused Carbazolesmentioning

confidence: 99%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

117

View full text Add to dashboard Cite

show abstract

“…4-Quinolinium-Indole Derivative (4QI). A microwave vessel was charged with a mixture of 1,4dimethylquinolinium iodide 48 (1.95 mmol), 1-(3-hydroxypropyl)indole-3-carboxyaldehyde 49 (1.62 mmol), 2 drops of piperidine, and 3 mL ethanol. The reaction mixture was exposed to microwave radiation using a CEM microwave reactor at 80 °C with stirring under variable pressure for 10 min.…”

Section: Journal Of the American Chemical Societymentioning

confidence: 99%

Ligand-Induced G-Quadruplex Polymorphism: A DNA Nanodevice for Label-Free Aptasensor Platforms

et al. 2019

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G-Quadruplexes (GQs) serve as popular recognition elements for DNA aptasensors and are incorporated into a DNA nanodevice capable of controlled conformational changes to activate a sensing mechanism. Herein we highlight the utility of a GQ−GQ nanodevice fueled by GQ-specific ligands as a label-free aptasensor detection strategy. The concept was first illustrated utilizing the prototypical polymorphic human telomeric repeat sequence (H-Telo22, d[AG3(T2AG3)3]) that can undergo ligand-induced topology changes between antiparallel, parallel, or hybrid GQ structures. The H-Telo22−ligand interactions served as a model of the GQ−GQ nanodevice. The utility of the device in a real aptasensor platform was then highlighted utilizing the ochratoxin A (OTA) binding aptamer (OTABA) that folds into an antiparallel GQ in the absence and presence of target OTA. Three cationic fluorogenic ligands served as GQ-specific light-up probes and as potential fuel for the GQ−GQ nanodevice by producing an inactive GQ topology (parallel or hybrid) of OTABA. Our findings demonstrate efficient OTAmediated dye displacement with excellent emission sensitivity for OTA detection when the fluorogenic dyes induce a topology change in OTABA (parallel or hybrid). However, when the fluorogenic dye fails to induce a conformational change in the antiparallel fold of OTABA, subsequent additions of OTA to the aptamer−dye complex results in poor dye displacement with weak emission response for OTA detection. These results are the first to exemplify a ligand-induced GQ−GQ nanodevice as an aptasensor mechanism and demonstrate diagnostic applications for topology-specific GQ binders.

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“…The pyrimidine-γ-carboline alkaloid ingenine B (isolated from an Indonesian sponge) exhibits a pronounced cytotoxicity against a murine lymphoma cell line [7] and several isocanthine analogs are effective against cervical cancer (HeLa cells) [8]. Moreover, γ-carbolines are known for their well-established DNA intercalating [9] and anti-Alzheimer [10] properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Dudhe

Krishnan

Yadav

et al. 2021

Beilstein J. Org. Chem.

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1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a–h and glycine alkyl esters 2a–c are shown to undergo a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted γ-carbolines 3aa–ea in good yields. The γ-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin, and kidney cancer cells.

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Intramolecular Diels–Alder reaction for the synthesis of tetracyclic carbazoles and isocanthines

Cited by 20 publications

References 17 publications

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Ligand-Induced G-Quadruplex Polymorphism: A DNA Nanodevice for Label-Free Aptasensor Platforms

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

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