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Stepanov A.I.,Special Design and Construction Bureau SDCB Technology | Astrat'ev A.A.,Special Design and Construction Bureau SDCB Technology | Sheremetev A.B.,RAS N. D. Zelinsky Institute of Organic Chemistry | Lagutina N.K.,Moscow State University | And 12 more authors.
European Journal of Medicinal Chemistry | Year: 2015

A series of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines (BIFAs) were prepared in good yields (60-90% for each reaction step) via a novel procedure from aminofurazanyl hydroximoyl chlorides and o-diaminobenzenes. The synthetic sequence was run under mild reaction conditions, it was robust and did not require extensive purification of intermediates or final products. Furthermore, there was no need for protection of reactive moieties allowing for the parallel synthesis of diverse BIFA derivatives. Subsequent biological evaluation of the resulting compounds revealed their anti-proliferative effects in the sea urchin embryo model and in cultured human cancer cell lines. The most active compounds showed 0.2-2 μM activities in both assay systems. The unsubstituted benzene ring of the benzoimidazole template as well as the unsubstituted amino group in the furazan ring were essential prerequisites for the antimitotic activity of BIFAs. Compound 57 bearing the 2-chlorophenyl acetamide substituent at the nitrogen atom of the imidazole ring was the most active molecule in the examined set. © 2015 Elsevier Masson SAS. Source


Stepanov A.I.,Special Design and Construction Bureau SDCB Technology | Dashko D.V.,Special Design and Construction Bureau SDCB Technology | Astrat'Ev A.A.,Special Design and Construction Bureau SDCB Technology
Chemistry of Heterocyclic Compounds | Year: 2013

The reduction of 3,4-bis(4-R-furazan-3-yl)furoxans with hydrazine or hydrogen in the presence of palladium on carbon resulted in opening of the furoxan ring and formation of (Z,E)-dioximes of 1,2-di(4-R-furazan-3-yl)ethane- 1,2-diones in high yield. The reactivity of the resultant glyoximes was studied. © 2013 Springer Science+Business Media New York. Source


Stepanov A.I.,Special Design and Construction Bureau SDCB Technology | Dashko D.V.,Special Design and Construction Bureau SDCB Technology | Astrat'Ev A.A.,Special Design and Construction Bureau SDCB Technology
Chemistry of Heterocyclic Compounds | Year: 2013

It was shown that the reduction of derivatives of 7-R-7H-tris[1,2,5] oxadiazolo[3,4-b:3′,4′-d:3″,4″-f]azepine 1-oxide by hydrazine hydrate or hydrogen in the presence of palladium on carbon is accompanied by opening of the furoxan ring of the starting compound to the two amino groups and leads to the production of 4-R-4H-bis[1,2,5]oxadiazolo[3,4-b: 3′,4′-f]azepine-8,9-diamines. Some chemical properties of the obtained diamino compounds are discussed. © 2013 Springer Science+Business Media New York. Source


Stepanov A.I.,Special Design and Construction Bureau SDCB Technology | Dashko D.V.,Special Design and Construction Bureau SDCB Technology | Astrat'ev A.A.,Special Design and Construction Bureau SDCB Technology
Central European Journal of Energetic Materials | Year: 2012

The results of our studies on the reactivity of 3,4-bis(4'-nitrofurazan-3'- yl)furoxan (BNFF), with some O- and N-nucleophiles are presented. It is shown that both nitro groups of BNFF can be easily replaced by nucleophiles. Depending on the identity of the nucleophile, BNFF may be transformed into two types of 1,2,5-oxadiazole derivatives, notably 4-R substituted bis(4-R-furazan-3-yl) furoxanes or 7-R substituted 7H(7R)-tris[1,2,5]oxadiazolo[3,4-b:3',4'-d:3",4"f] azepine-1-oxides - a new heterocyclic system comprised of an azepine ring annelated with three 1,2,5-oxadiazole rings. Source


Astrat'Ev A.A.,Special Design and Construction Bureau SDCB Technology | Dashko D.V.,Special Design and Construction Bureau SDCB Technology | Stepanov A.I.,Special Design and Construction Bureau SDCB Technology
Central European Journal of Chemistry | Year: 2012

The nucleophilic displacement of two nitro groups in 3,4-bis(3- nitrofurazan-4-yl)furoxan with ammonia, primary aliphatic amines and hydrazine leads to formation of a novel heterocyclic system, 7H-tris[ 1,2,5]oxadiazolo[3, 4-b:3',4'-d:3'',4''-f]azepine. The reaction of compound 1 with secondary aliphatic amines proceeds in a typical way for nitrofurazans when the nitro-group in the starting compound is substituted by RR'N-group. © Versita Sp. z o.o. Source

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