2-(Fluoro-) and 2-(methoxyanilino)-1,4-naphthoquinones. Synthesis and mechanism and effect of fluorine substitution on redox reactivity and NMR

Leyva, Elisa; Baines, Kim M.; Espinosa‐González, Claudia G.; Magaldi-Lara, Diego A.; Loredo‐Carrillo, Silvia E.; Luna-Méndez, Telma A. De; López, Lluvia I.

doi:10.1016/j.jfluchem.2015.08.016

Cited by 15 publications

(7 citation statements)

References 14 publications

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“…Successful results on the use of the Ce(III) catalyst in the oxidative amination reaction of quinones with arylamines have been reported in literature [ 32 – 38 ]. These acid catalysts probably increase the electrophilic character of the enone system of the quinones, via coordination with the oxygen atom of the carbonyl group, thus promoting the Michael-type addition [ 35 , 39 , 40 ].…”

Section: Resultsmentioning

confidence: 99%

“…The acid-induced formation of the arylation compounds 16-28 from acylquinones 9-15 and their reaction with N , N -dimethylaniline are proposed to occur according to the mechanism of reaction depicted in Scheme 3 . This approach is based on the reaction mechanism for the Ce(III)-promoted phenylamination reaction of 1,4-naphthoquinone with 2-fluoro- and 2-methoxyanilines reported by Leyva et al [ 35 ]. Initially, a selective conjugate Michael-type addition of the arylamine across the enone system C 3 =C 2 -C 1 =O seems plausible.…”

Section: Resultsmentioning

confidence: 99%

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New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

Ríos

Valderrama

Cautin

et al. 2020

Oxidative Medicine and Cellular Longevity

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The reaction of 2-acyl-1,4-naphthoquinones with N,N-dimethylaniline and 2,5-dimethoxyaniline, promoted by catalytic amounts of CeCl3·7H2O under “open-flask” conditions, produced a variety of 2-acyl-3-aminophenyl-1,4-naphthoquinones structurally related to the cytotoxic 2-acetyl-3-phenyl-1,4-naphthoquinone, an inhibitor of the heat shock chaperone protein Hsp90. The members of the 2-acyl-3-aminophenyl-1,4-naphthoquinone series were isolated in good yields (63-98%). The cyclic voltammograms of the 2-acyl-3-aminophenyl-1,4-naphthoquinone exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasireversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series are sensitive to the push-pull electronic effects of the substituents in the naphthoquinone scaffold. Furthermore, the in vitro antiproliferative properties of these new quinones were evaluated on two human cancer cells DU-145 (prostate) and MCF-7 (mammary) and a nontumorigenic HEK-293 (kidney) cell line, using the MTT colorimetric method. Two members, within the series, exhibited interesting cytotoxic activities on human prostate and mammary cancer cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

Ríos

Valderrama

Cautin

et al. 2020

Oxidative Medicine and Cellular Longevity

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“…The aromatic proton H(5) takes part intermolecular C–H···O interaction ( Table 2 ) in most of the crystal structures of known derivatives; if such interactions exist in the solution, the chemical shift variation is expected. The 1 H chemical shift was observed at ~ δ = 7.8–7.9 ppm in all compounds; this implies that the intermolecular C–H···O interaction does not directly affect its chemical shift [ 45 ]. A similar inference for the 1 H chemical shift of other benzenoid ring protons H(8), H(6), and H(7) can be drawn.…”

Section: Resultsmentioning

confidence: 99%

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Patil

Jadhav

Salunke‐Gawali

et al. 2021

Heliyon

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1 H as well as 13 C chemical shifts of 32 compounds of C (3) substituted 2-( n -alkylamino)-3R-naphthalene-1,4-dione (where n -alkyl: methyl, to octyl, R = H, Cl, Br, and CH 3 ) are investigated through 1 H, 13 C, DEPT, gDQCOSY, and gHSQCAD NMR experiments and M06-2X/6-311++G (d,p) density functional theory are discussed. Single crystal X-ray structure of Br-3, as well as 18 different derivatives of naphthalene-1,4-diones, are revealed for its inter and intra-molecular hydrogen bonding interactions.

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“…It is not possible to separate the ortho and para isomers. The substituted naphthoquinones were prepared by the method reported in the literature with several modifications [40,41].…”

Section: Synthesizedmentioning

confidence: 99%

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Leyva,

Loredo-Carrillo,

Aguilar

2023

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Nitrated products are important since they are intermediates in the synthesis of other compounds, such as explosives, perfumes, dyes and plastics, among others, and they have an easy capacity to convert into other functional groups. The synthesis of compounds with biological activity that have a nitro group in their structure is relevant to improving and/or enhancing their effect. In this work, different methodologies for the nitration of naphthoquinone derivative compounds are presented. The nitration of 3-R-2-(phenylamino)-1,4-naphthoquinone derivatives was carried out with nitric acid and sulfuric acid; milder reaction conditions were also established by diluting the acids or performing the reaction with weaker acids. Other methodologies were tested using nitrate salts for mononitrate product synthesis. We used a solvent-free reaction with oxalic acid using 3-R-2-(phenylamino)-1,4-naphthoquinones (R=H, Br or Cl), noting that the electronegativity of the chlorine group is decisive for achieving nitration with good yields. Finally, a Michael addition was performed with some nitrated anilines. To obtain denitrated compounds in the ortho and para positions, the reaction with strong acids is feasible; however, for the formation of mononitrated products, the Michael-type addition is more convenient.

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2-(Fluoro-) and 2-(methoxyanilino)-1,4-naphthoquinones. Synthesis and mechanism and effect of fluorine substitution on redox reactivity and NMR

Cited by 15 publications

References 14 publications

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

1H and 13C NMR chemical shifts of 2-n-alkylamino-naphthalene-1,4-diones

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

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