Nucleophilic substitution reactions of 1,4-naphthoquinone and biologic properties of novel S-, S,S-, N-, and N,S-substituted 1,4-naphthoquinone derivatives

Ibis, Cemil; Tuyun, Amaç Fatih; Bahar, Hrisi; Ayla, Sibel Sahınler; Stasevych, Maryna; Musyanovych, Rostyslav Ya.; Komarovska‐Porokhnyavets, Olena; Novikov, Volodymyr

doi:10.1007/s00044-013-0806-y

Cited by 35 publications

(21 citation statements)

References 19 publications

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“…1 M, 15 showed behaviour typical of quinones in aprotic medium. 29,30 Two reversible one-electron waves were observed. The first reversible reduction wave was, for 1, −0.287 V vs. Ag/AgCl, represented the addition of one electron to the quinone core to form a semiquinone anion radical.…”

Section: Electrochemical Studymentioning

confidence: 99%

“…Drawings were performed with the program ORTEP-III 21 (499.74 MHz, CDCl 3 ): δ = 0.8 (t, J = 7.32 Hz, 3H, CH 3 ), 1.2-1.4 (m, 2H, CH 2 ), 1.6-1.7 (m, 2H, N-CH 2 -CH 2 ), 2.9 (t, J = 6.81 Hz, 2H, N-CH 2 -CH 2 ), 3.3 (t, J = 7.81 Hz, 2H, S-CH 2 ), 3.5 (t, J = 6.84 Hz, 2H, N-CH 2 ), 7.50 (t, J = 7.32 Hz, 1H, H arom ), 7.55 (t, J = 7.81 Hz, 1H, H arom ), 7.85 (dd, J = 6.84 Hz, J = 6.85 Hz, 1H, H arom ), 7.95 ppm (dd, J = 7.32 Hz, J = 6.84 Hz, 1H, H arom ). 13 [3,3 ]-bis (1,4- 2.5g 7,8,9,10,11,12,13,14,23,24,25,26,27,28,29,…”

Section: Crystal Structure Determination and Refinementmentioning

confidence: 99%

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Synthesis, characterization of N-, S-, O-substituted naphtho- and benzoquinones and a structural study

Ibis

Deniz

2012

J Chem Sci

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The new series of N-, SO O-substituted 1,4-naphthoquinone and SO O-substituted 1,4benzoquinone compounds were synthesized via vinylic substitution. Compounds 3 and 4 were synthesized from the reaction of 1 with 2. Compounds 6, 7 and 8 were synthesized from reaction of 1 with 5. Compounds 10 and 11 were obtained from the reaction of 1 with 9. Compounds 13 and 14 were synthesized from the reaction of 1 with 12. Compounds 16 and 17 were obtained from the reaction of 15 with 2. Photochemical and electrochemical properties of N-, SO O-substituted quninone compounds were determined by using fluorescence spectroscopy and cyclic voltammetry. Crystal structure of 2-(7-sulphanyl-4-methyl-coumarinyl)-3-(1-ethoxy)-1,4-naphthoquinone 13 was determined by X-ray diffraction method.

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Section: Electrochemical Studymentioning

confidence: 99%

Section: Crystal Structure Determination and Refinementmentioning

confidence: 99%

Synthesis, characterization of N-, S-, O-substituted naphtho- and benzoquinones and a structural study

Ibis

Deniz

2012

J Chem Sci

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“…Важливе місце серед похідних піразолів займають амінопіразоли. Наявність аміногрупи та інших функціональних груп у піразольному кільці уможливлює подальшу модифікацію молекули, розроблення нових методик синтезу функціоналізованих похідних піразолу і дослідження їхніх властивостей [4][5][6]10].…”

Section: вступunclassified

Synthesis and Prediction of the Biological Activity of Heterocyclic N-Derivatives Naphthoquinone

Polish¹,

Марінцова²,

Журахівська³

et al. 2019

CTAS

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“…In recent years, the interest in studying naphthoquinones has intensified, both for its relevance in vital biochemical processes, as well as for its variety of known pharmacological properties, such as anti-inflammatory [4,5], antitumor [6,7], antibacterial, antifungal [8], antiviral [7,9,10], antimalarial [11], leishmanicidal [12], and trypanocidal activities [13][14][15]. Among the naphthoquinone compounds included in the quinone family, there is the IVS320 molecule (Figure 1a), chemically named 3a,10bdihydro-1H-cyclopenta [b]naphtho [2,3-d]furan-5,10-dione, produced synthetically and with proven antifungal [16] and antichagasic activity [17].…”

Section: Introductionmentioning

confidence: 99%

Novel Solid Dispersions of Naphthoquinone Using Different Polymers for Improvement of Antichagasic Activity

et al. 2020

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IVS320 (3a,10b-dihydro-1H-cyclopenta[b]naphtho[2,3-d]furan-5,10-dione) is a naphthoquinone that has low solubility in aqueous medium, a physical behavior that limits its biological activities, considering that compounds from this class have several activities. In this work, solid dispersions (SDs) prepared between IVS320 and polymers hydroxypropyl methylcellulose (HPMC), polyethylene glycol (PEG), and polyvinylpyrrolidone (PVP) were developed using physical mixture (PM), kneading (KN), and rotary evaporation (RE) methods. Dispersions were investigated using Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermogravimetry (TG), powder X-ray diffraction (PXRD), and scanning electron microscopy (SEM). In addition, in vitro antiparasitic activity in Trypanosoma cruzi Y strains was evaluated. Physical-chemical characterization demonstrated the formation of SDs through the interaction of IVS320 with polymeric matrices. SDs of IVS320-polymer presented a significant potentiation of antichagasic activity, with inhibitory growth around 62% (IVS320-HPMC/RE), 55% (IVS320-PEG/RE), and 85% (IVS320-PVP/RE), while pure IVS320 showed a value of 48% for the highest concentrations evaluated (50 µg/mL).

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Nucleophilic substitution reactions of 1,4-naphthoquinone and biologic properties of novel S-, S,S-, N-, and N,S-substituted 1,4-naphthoquinone derivatives

Cited by 35 publications

References 19 publications

Synthesis, characterization of N-, S-, O-substituted naphtho- and benzoquinones and a structural study

Synthesis, characterization of N-, S-, O-substituted naphtho- and benzoquinones and a structural study

Synthesis and Prediction of the Biological Activity of Heterocyclic N-Derivatives Naphthoquinone

Novel Solid Dispersions of Naphthoquinone Using Different Polymers for Improvement of Antichagasic Activity

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