Synthesis of New ‘Hybrid’ Compounds Based on Benzofuroxans and Aminoalkylnaphthalimides

Chugunova, Elena; Mukhamatdinova, Rezeda E.; Сазыкина, М. А.; Dobrynin, A. B.; Сазыкин, И. С.; Karpenko, Alexander S.; Mirina, Elena; Zhuravleva, M. V.; Гаврилов, Н. В.; Karchava, Shorena; Бурилов, А. Р.

doi:10.1111/cbdd.12685

Cited by 8 publications

(5 citation statements)

References 16 publications

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“…As in the previously illustrated examples [12,13], the obtained results indicate that the reactivity of two chlorine atoms in benzofuroxan 1 towards nucleophilic substitution differs significantly. The substitution occurred in the position 4 of the benzofuroxan 1 solely regardless of the reactants ratio, reaction time and the temperature.…”

Section: Synthesissupporting

confidence: 81%

“…Molecular modification is a rather promising strategy in the development of drug analogues with better bioavailability, higher biological activity, and less toxicity. Special attention is currently paid to the "hybrid" compound containing benzofuroxan and another biologically active subunit in one molecule [3,12,13]. Evaluation in vitro and in vivo of levels of prostaglandin E2 and thromboxane B2 decrease in the blood plasma samples of a compound obtained by binding of diclofenac and benzofuroxan fragments showed that after adding of benzofuroxan scaffold, this compound retains the pharmacological characteristics of Diclofenac, including anti-inflammatory activity, without the deleterious gastrointestinal effects which is normally present in the prototype [14].…”

Section: Introductionmentioning

confidence: 99%

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Design of Novel 4-Aminobenzofuroxans and Evaluation of Their Antimicrobial and Anticancer Activity

Chugunova

Газизов

Сазыкина

et al. 2020

IJMS

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A series of novel 4-aminobenzofuroxan derivatives containing aromatic/aliphatic amines fragments was achieved via aromatic nucleophilic substitution reaction of 4,6-dichloro-5-nitrobenzofuroxan. The quantum chemistry calculations were performed to identify the factors affecting the regioselectivity of the reaction. The formation of 4-substituted isomer is favored both by its greater stability and the lower activation barrier. Antimicrobial activity of the obtained compounds has been evaluated and some of them were found to suppress effectively bacterial biofilm growth. Fungistatic activity of 4-aminobenzofuroxans were tested on two genetically distinct isolates of M. nivale. The effect of some benzofuroxan derivatives is likely to be more universal against different varieties of M. nivale compared with benzimidazole and carbendazim. Additionally, their anti-cancer activity in vitro has been tested. 4-aminofuroxans possessing aniline moiety showed a high selectivity towards MCF-7 and M-HeLa tumor cell lines. Moreover, they exhibit a significantly lower toxicity towards normal liver cells compared to Doxorubicin and Tamoxifen. Thus, benzofuroxans containing aromatic amines fragments in their structure are promising candidates for further development both as anti-cancer and anti-microbial agents.

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Section: Synthesissupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Design of Novel 4-Aminobenzofuroxans and Evaluation of Their Antimicrobial and Anticancer Activity

Chugunova

Газизов

Сазыкина

et al. 2020

IJMS

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“…Additional studies were performed on these samples by means of bioluminescent bioreporter E. coli (Lux) strains in order to assess the ability of these solid catalysts to generate mutagenic species and/or cytotoxic ROS (Chugunova et al, 2015(Chugunova et al, , 2016.…”

Section: Decontamination From Blistering and Nerve Agent Simulantsmentioning

confidence: 99%

“…Finally, aiming at a real on-field use, where a total-loss dispersion of solid decontamination mixtures is likely, the potential impact of the catalysts on the environment was evaluated by three main kinds of biotests, as rapid, costeffective and sensitive screening tools: (i) the marine bioluminescent bacterium, P. leiognathi Sh1, isolated from Azov Sea, was utilised as a target organism to assess the direct toxic impact on living organisms (Katsev, 2014;Kuryanov, Chupakhina, Shapovalova, Katsev, & Chirva, 2011); (ii) the potential mutagenic properties of the solids and their ability to generate toxic oxygen radicals were evaluated by luminescent bioreporter strains of Escherichia coli MG1655, with the lux CDABE operon from Photorhabdus luminescens (Chugunova et al, 2016(Chugunova et al, , 2015Zavilgelsky, Kotova, Yu, & Manukhov, 2007); and (iii) the potential detrimental impact of the solids on vegetable plants was evaluated by studying the effects on the chlorophyll fluorescence and on germination parameters on P. vulgaris L., as a model plant (common bean plants) (Maxwell & Johnson, 2000).…”

Section: Introductionmentioning

confidence: 99%

Tungsten oxide: a catalyst worth studying for the abatement and decontamination of chemical warfare agents

Costenaro

Bisio

Carniato

et al. 2017

Global Security: Health, Science and Policy

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Tungsten(VI) oxide, WO 3 , was studied and used as a heterogeneous catalyst for the liquid-phase oxidative abatement and solid-phase decontamination of simulants of chemical warfare agents, CWAs. The catalytic performance of WO 3 was compared to the one of a soluble W-containing model catalyst, W(IV)-heptaisobutyl polyhedral oligomeric silsesquioxane, W-POSS. In liquid-phase abatement tests, WO 3 promoted a complete degradation of the toxic agent simulant within 24 h, in the presence of aqueous hydrogen peroxide, at room temperature. In solid-phase decontamination tests, when WO 3 was mixed with sodium perborate as a solid oxidant, it was also tested in the decontamination of a cotton textile support from organosulfide and organophosphonate agents (simulants of blistering and nerve CWAs, respectively), showing promising performances comparable to, or sometimes better than, a nanostructured TiO 2 catalyst, taken as a reference material. The environmental impact of the WO 3 catalyst was assessed on bioluminescent Photobacterium leiognathi Sh1 bacteria, over which no acute nor chronic detrimental effects were recorded. Then, when in contact with a vegetable species such as Phaseolus vulgaris L. (common bean), WO 3 did not cause damage to the photosynthetic apparatus of the plant, whereas a clear inhibition of the seed germination was evidenced.

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“…Over the past decades, a huge number of benzofuroxan derivatives have been studied and described, which show a wide range of biological activity [ 5 , 6 , 7 , 8 ]. The synthetic potential of benzofuroxans is determined by the easiness of introducing into their structure, while maintaining the furoxan ring, various pharmacophore groups responsible for the appearance of biological activity, as well as obtaining on their basis a wide range of different classes of NO-containing heterocyclic compounds [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Water-Soluble Salts Based on Benzofuroxan Derivatives—Synthesis and Biological Activity

Chugunova

Matveeva

Tulesinova

et al. 2022

IJMS

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A series of novel water-soluble salts of benzofuroxans was achieved via aromatic nucleophilic substitution reaction of 4,6-dichloro-5-nitrobenzofuroxan with various amines. The salts obtained showed good effectiveness of the pre-sowing treatment of seeds of agricultural crops at concentrations of 20–40 mmol. In some cases, the seed treatment with salts leads not only to improved seed germination, but also to the suppression of microflora growth. Additionally, their anti-cancer activityin vitrohas been researched. The compounds with morpholine fragments or a fragment of N-dimethylpropylamine, demonstrated the highest cytotoxic activity, which is in good correlation with the ability to inhibit the glycolysis process in tumor cells. Two compounds 4e and 4g were selected for further experiments using laboratory animals. It was found that the lethal dose of 50% (LD50) is 22.0 ± 1.33 mg/kg for 4e and 13.75 ± 1.73 mg/kg for 4g, i.e., compound 4e is two times less toxic than 4g, according to the mouse model in vivo. It was shown that the studied compounds exhibit antileukemia activity after a single intraperitoneal injection at doses from 1.25 to 5 mg/kg, as a result of which the average lifespan of animals with a P388 murine leukemia tumor increases from 20 to 28%. Thus, the water-soluble salts of benzofuroxans can be considered as promisingcandidates for further development, both as anti-cancer agents and as stimulants for seed germination and regulators of microflora crop growth.

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Synthesis of New ‘Hybrid’ Compounds Based on Benzofuroxans and Aminoalkylnaphthalimides

Cited by 8 publications

References 16 publications

Design of Novel 4-Aminobenzofuroxans and Evaluation of Their Antimicrobial and Anticancer Activity

Design of Novel 4-Aminobenzofuroxans and Evaluation of Their Antimicrobial and Anticancer Activity

Tungsten oxide: a catalyst worth studying for the abatement and decontamination of chemical warfare agents

Water-Soluble Salts Based on Benzofuroxan Derivatives—Synthesis and Biological Activity

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