Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives*

Ферштат, Леонид Л.; Epishina, Margarita A.; Kulikov, Alexander S.; Стручкова, Марина И.; Махова, Нина Н.

doi:10.1007/s10593-015-1678-5

Cited by 35 publications

(6 citation statements)

References 27 publications

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“…Interestingly, most of the 4‐nitrofuroxans do not cleave under the action of thiolate anions, but undergo nucleophilic substitution of the nitro group, resulting in stable sulfonylfuroxan derivatives . A similar trend is observed in the reaction of nitrofuroxans with other types of heteroatom nucleophiles …”

Section: Synthesis No‐donor Properties and Pharmacological Activitsupporting

confidence: 79%

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Ферштат

Махова

2017

ChemMedChem

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The molecular hybridization of different compounds with known pharmacological activity is a particularly prominent approach for the design of potential drugs with improved pharmacokinetic profiles. Much attention over the last decade has been focused on the synthesis of hybrid structures with a nitric oxide (NO)-donor framework, as NO is a ubiquitous and crucial regulator of cellular metabolism, affecting various physiological and pathophysiological processes. 1,2,5-Oxadiazole 2-oxides (furoxans), which are capable of exogenous NO release in the presence of thiol cofactors, are an important class of prospective NO donors. As such, a wide range of hybrid compounds that combine a furoxan ring with various pharmacologically active structures have been created. This review focuses on recent results in the synthesis and pharmacological activity of furoxan-based hybrids. Special attention is given to chemo- and regioselective methods used in the preparation of these hybrid structures, and the role of synergistic effects on their pharmacological activity, associated with the furoxan fragment.

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Section: Synthesis No‐donor Properties and Pharmacological Activitsupporting

confidence: 79%

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Ферштат

Махова

2017

ChemMedChem

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“…The reaction of hetarylthiols with 4-nitrofuroxan to form C–S bonds on the furoxan ring has recently been reported (Scheme 15a). 34,43 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was the base of choice. Due to the wide availability of substrate 4-nitrofuroxans, 25 a compound library of hetarylsulfanyl furoxans was readily generated using this method.…”

Section: Furoxan Synthesis Based On Prismentioning

confidence: 99%

Recent progress in synthesis and application of furoxan

Yousef

Matsubara

2023

RSC Adv.

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“…A series of novel heterocyclic structures containing poly-nitrogen or nitrogen-oxygen heterocycles attached to a furoxan ring either directly or by means of heteroatom bridges: 4-hetaryloxyfuroxans 27 1, (1,2,4-oxadiazol-3-yl)furoxans 28 2, (1,2,4-triazin-3-yl)furoxans 29 3 and nitrobifuroxanyl ensembles 30 4, was available.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring

Larin¹,

Ферштат²,

Аникина³

et al. 2017

Arkivoc

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A direct approach to the synthesis of previously unknown 1H-1,2,3-triazolylfuroxans, involving nucleophilic substitution of the nitro group in nitrofuroxans followed by catalytic [3+2] cycloaddition of intermediate azidofuroxans to 1,3-ketoesters, is reported. The scope of the triazolylfuroxans was additionally diversified through a number of transformations of the functional groups attached to the 1,2,3-triazole ring. The cytotoxic activity of the newly synthesized triazolylfuroxans and of previously reported hetarylfuroxans was studied. The NO-donor capability of selected synthesized hetarylfuroxans was measured by the Griess reaction using a spectrophotometric technique.

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Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives*

Cited by 35 publications

References 27 publications

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs

Recent progress in synthesis and application of furoxan

Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring

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