Advances in the chemistry of monocyclic amino- and nitrofuroxans

Махова, Нина Н.; Kulikov, Alexander S.

doi:10.1070/rc2013v082n11abeh004369

Cited by 41 publications

(11 citation statements)

References 88 publications

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“…Notably, the reaction with furoxan 11 proceeds chemoselectively only at C4 of the furoxan ring. This is a general tendency in furoxan chemistry according to which the C4 atom is more electrophilic than C3 . Bis(phenylsulfonyl)furoxan 11 was obtained through a three‐step sequence from thiophenol (Scheme ) .…”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

“…Furoxans 11 , 16 a , and isomeric 4‐nitrofuroxan 15 b , synthesized by several methods depicted in Scheme , constitute a class of good inhibitors of thioredoxin glutathione reductase, an important enzyme in flatworm parasites . The synthesis of 4‐nitrofuroxan 15 b is based on the domino reaction of unsaturated compounds (styrene or 2‐phenylacrylic acid).…”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

“… Various routes to 4‐nitro‐3‐phenylfuroxan 15 b . Reagents and conditions : a) X=H: NaNO 2 , CH 2 Cl 2 , AcOH, RT, 2 h, then HCl, overnight, 68 %; b) X=COOH: NaNO 2 , AcOH, RT, 72 h, 36 %.…”

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

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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 Activitmentioning

confidence: 99%

Section: Synthesis No‐donor Properties and Pharmacological Activitmentioning

confidence: 99%

See 1 more Smart Citation

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

Ферштат

Махова

2017

ChemMedChem

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“…Recent scientific investigations of our laboratory were directed towards the synthesis and reactivity of nitrogen-oxygen containing heterocycles -1,2,5-oxadiazole 2-oxides (furoxans). 3,4 Furoxans are unique representatives of heterocyclic compounds. On the one hand they are of interest as high energy compounds due to a positive enthalpy of formation and the presence of two active oxygen atoms in the molecule.…”

Section: Introductionmentioning

confidence: 99%

“…42,43 The advantage of this method is that it yields only one of the two possible regioisomers of the 1,2,3-triazoles with unsymmetrically substituted substrates and safe amines are used instead of dangerous azido derivatives. Since aminofuroxans are rather available compounds, 3 we aimed to develop new, regioselective method for the synthesis of (1H-1,2,3-triazol-1-yl)furoxans 1 by an interaction of 4-aminofuroxans 2 with diazo-β-dicarbonyl compounds 3.…”

Section: Introductionmentioning

confidence: 99%