Heterocyclic Quinones

Tisšler, Miha

doi:10.1016/s0065-2725(08)60329-3

Cited by 34 publications

(7 citation statements)

References 796 publications

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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%

“…The antitumor activity and DNA affinity of amino-substituted quinones is well established, [1][2][3][4] and several drugs in this category have seen utility in the cancer clinic; for example, mitomycin (1), 5,6 ametantrone (2), 7 mitoxantrone (3), 8,9 pixantrone (4), [10][11][12] and WEHI-150 (5) 13,14 (Figure 1).…”

Section: Introductionmentioning

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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Section: Resultsmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

See 1 more Smart Citation

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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“…The chemistry of quinones is largely dependent on the substituent being either on the quinonic or on adjacent rings. This is reflected in their chemical reactivity, especially in heterocyclic quinones [8]. Hydroxylated quinones that have one or more hydroxy groups attached directly to the quinone moiety are found in Nature in great variety.…”

Section: Resultsmentioning

confidence: 99%

Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity

2013

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Abstract:The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy's salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line.

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“…The chemistry of quinones is largely dependent on the substituents being either on the quinonic or on adjacent rings. This is reflected in their chemical reactivity, especially in heterocyclic quinines [2]. A Schiff base is a nitrogen analogue of an aldehyde or ketone in which the C=O group is replaced by C=N-R group.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and DFT Calculations of 4-((2-Hydroxyethyl)imino)naphthalen-1(4H)-One and its Cu(II) Complex

Görgülü

Dede

2018

Acta Phys. Pol. A

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We have reported herein the synthesis of a novel quinone derivative ligand containing the Schiff base and its Cu(II) complex starting from 1,4-naphthoquinone. Synthesized compounds were characterized using the Fourier transform infrared, UV-Vis, elemental analysis, inductively coupled plasma optical emission spectrometry, molar conductivity, and magnetic susceptibility measurements. The free ligand was also characterized by 1 H-and 13 C-NMR spectra. Elemental analyses, stoichiometric and spectroscopic data indicated that the metal:ligand ratio is 1:2 and octahedral structure is proposed for the metal complex of the Schiff base ligand. Computational quantum calculations were also performed using DFT/B3LYP level of theory with 6-311++G(d,p) basis set for the synthesized ligand. It was found that the experimental and theoretical spectroscopic data were consistent.

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Heterocyclic Quinones

Cited by 34 publications

References 796 publications

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

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

Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity

Synthesis, Characterization and DFT Calculations of 4-((2-Hydroxyethyl)imino)naphthalen-1(4H)-One and its Cu(II) Complex

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