The synthesis of 7,8,9,10-tetrafluoroellipticine

Gruver, E. James; Onyango, Evans O.; Gribble, Gordon W.

doi:10.24820/ark.5550190.p010.414

Cited by 4 publications

(7 citation statements)

References 28 publications

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“… [17–21] Moreover, those multistep reactions often require non‐readily available fluorine‐containing substrates [22–24] . On the other hand, single fluorine atom substitutions are a rare class of tetrafluoroarene synthetic method and demand properly functionalized pentafluorobenzenes (Figure 1, II) [25–31] …”

Section: Introductionmentioning

confidence: 99%

Conversion of Ketones into Blue‐Emitting Electron‐Deficient Benzofurans

Górski

Ostojić

Banasiewicz

et al. 2023

Chemistry A European J

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A novel heavy metal-free and safe synthetic methodology enabling one-step conversion of ketones into corresponding 4,5,6,7-tetrafluorobenzofurans (F 4 BFs) has been developed. The presented approach has numerous advantageous qualities, including utilization of readily available substrates, broad scope, scalability, and good reaction yields. Importantly, some of the benzofurans prepared by this method were heretofore inaccessible by any other known transformation. Importantly, furo[2,3-b]pyrazines and heretofore unexplored difuro[2,3-c:3',2'-e]pyridazine can be prepared using this strategy. Spectroscopic studies reveal that for simple systems, absorption and fluorescence maxima fall within the UV spectral range, while π-electron system expansion red-shifts both spectra. Moreover, the good fluorescence quantum yields observed in solution, up to 96 %, are also maintained in the solid state. Experimental results are supported by density functional theory (DFT) calculations. The presented methodology, combined with the spectroscopic characteristics, suggest the possibility of using F 4 BFs in the optoelectronic industry (i. e., organic light emitting devices (OLED), organic field-effect transistors (OFET), organic photovoltaics (OPV)) as inexpensive and readily available emissive or semiconductor materials.

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Section: Introductionmentioning

confidence: 99%

Conversion of Ketones into Blue‐Emitting Electron‐Deficient Benzofurans

Górski

Ostojić

Banasiewicz

et al. 2023

Chemistry A European J

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“…The [2,7]naphthyridine-5,12-diones (18a-d) were synthesized from 1-(phenylsulfonyl)indole (20) as shown in Scheme 2. The synthesis of bromo indoloquinone (24) parallels our earlier synthesis of indoloquinone 6.…”

Section: Resultsmentioning

confidence: 99%

“…We have previously synthesized and utilized the indolo [1,2-b] [2,7]naphthyridine-5,12-dione (6) ring system to forge several members of the 6H-pyrido [4,3-b]carbazole family of antitumor alkaloids, including ellipticine (7), 9-methoxyellipticine (8), olivacine (9), 13-oxoellipticine (10), 7,8,9,10-tetrafluoroellipticine (11), and ellipticine quinone (12) [15][16][17][18][19][20] (Figure 2). A variation of our method allowed for the synthesis of 10Hpyrido [2,3-b]carbazoles (13) 21 and 6,11-disubstituted-benzo[b]carbazoles (14).…”

Section: Figurementioning

confidence: 99%

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Synthesis and DNA binding of 6-(alkylamino)indolo[1,2-b][2,7]naphthyridine-5,12-quinones

Davis¹,

Cory²,

Fairley³

et al. 2019

Arkivoc

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“…Generally, synthetic strategies leading to the target molecule are classified according to assembly of the last ring as B, C, D, and B + C types (Passemar et al, 2011) [10] (see Figure 1). Among the different synthetic routes available [21][22][23][24][25][26][27][28][29], the method originally proposed by Cranwell and Saxton appears to be the most practical one [21,30]. It consists of a five-stage ''D-type'' procedure starting from appropriately substituted indoles or carbazoles.…”

Section: Introductionmentioning

confidence: 99%

Indole alkaloid ellipticine as efficient multitarget compound

et al. 2022

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First isolated from the tropical plant Oschrosia elliptica, indole alkaloid ellipticine provoked huge interest since it demonstrated antitumor activity was demonstrated along with limited toxic side effects and a complete lack of hematological toxicity. In this work, a five-step Cranwell and Saxton synthesis was used for obtaining ellipticine (Ell). Ellipticine hydrochloride salt (Ell×HCl) was also synthesized. Detailed in vitro studies of anticancer, antimalarial, and leishmanicidal activities were performed. Antiproliferation assay using DU145 cancer cell line treated with Ell showed a consistent reduction in cell proliferation and cell viability when treated with 5 μmol Ell. Anti-proliferation activity was more pronounced for the Ell×HCl solutions. Both the Ell and Ell×HCl revealed moderate activity in vitro against Leishmania amazonensis promastigotes, which is related to insufficient solubility of the drugs. IC50 values of Ell and Ell×HCl were determined in vitro against multidrug resistant Plasmodium falciparum strain K1. The Ell×HCl was shown to be almost three times more potent than the Ell in DMSO. Upon dilution with water, Ell solubility and activity drops down, while the activity and solubility of Ell×HCl is enhanced up to 10 times in 50:50 aqueous DMSO solutions

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The synthesis of 7,8,9,10-tetrafluoroellipticine

Cited by 4 publications

References 28 publications

Conversion of Ketones into Blue‐Emitting Electron‐Deficient Benzofurans

Conversion of Ketones into Blue‐Emitting Electron‐Deficient Benzofurans

Synthesis and DNA binding of 6-(alkylamino)indolo[1,2-b][2,7]naphthyridine-5,12-quinones

Indole alkaloid ellipticine as efficient multitarget compound

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