L. V. Batog

Synthesis of nitro, nitroso, azo, and azido derivatives of (4-R1-5-R2-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles by oxidation and diazotization of the corresponding amines

Nitro-, nitroso-, and azo-1,2,5-oxadiazoles with 4-R1-5-R2-1,2,3-triazol-1-yl substituents were synthesized by oxidation of amino-(1,2,3-triazol-1-yl)-1,2,5-oxadiazoles (aminotriazolylfurazans). Azido-1,2,5-oxadiazole was prepared by diazotization of amino(triazolyl)furazan followed by treatment of the diazonium salt with sodium azide. Depending on the nature of the substituents and the reagent, triazolylfurazans can undergo destruction to give amino-R-furazans (R = NO2, N3, aminofurazanylazo), the amino group being formed from the triazole ring.

Oxidative macrocyclocondensation of 3,4-diaminofurazan and 4,4′-diamino-3,3′-azofurazan with dibromoisocyanurate. Crystal structures of hexa- and octadiazenofurazan macrocycles

The oxidative cyclocondensation of 3,4-diaminofurazan and 4,4′-diamino-3,3′-azofurazan with dibromoisocyanurate afforded macrocyclec polydiazenofurazans. The reaction can be directed towards the formation of both the four-membered cycle alone or the three-, six-, and eight-membered macrocycles.

Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

Methods for the synthesis of amino(1,2,3-triazol-1-yl)-1,2,5-oxadiazoles (amino-triazolylfurazans) with CH2Cl and COCH2Br substituents in the triazole ring were developed and nucleophilic substitution for their halogen atom in reactions with N-, O-, and S-nucleophiles were studied. The possibility of displacing the NO2 group from the furazan and triazole rings in triazolylfurazans by an azido group was investigated. Novel compounds of this series were synthesized; the reaction rate and pathway were found to depend on the nature of the substrate and the reagent and the position of the substituent in isomers.

Synthesis of (1,2,3-triazol-1-yl)furazans. 2. Reaction of azidofurazans with morpholinonitroethene

We have studied the 1,3-dipolar cycloaddition of azidofurazans to morpholinonitroethene and prepared 1,2,3-triazoles with furazan ring in position 1 and NO2 group at position 4.

Novel method for synthesis of 3,4:7,8:11,12:15,16-tetrafurazano-1,2,5,6,9,10,13,14-octaazacyclohexadeka-1,3,5,7,9,11,13,15-octaene and its crystal structure

We have established the formation of a tetradiazenofurazan macrocycle as a result of intramolecular oxidative cyclization of 4,4′-bis(4-aminofurazanyl-3-azo)-3,3′-azofurazan and have studied its crystal structure.

Synthesis of 4-R-3-(4-R1-5-R2-1,2,3-triazol-1-YL)furazans. 1. Azidofurazans in 1,3-dipolar cycloaddition reactions with substituted acetylenes

The 1,3-dipolar cycloaddition of azidofurazans to substituted acetylenes has been studied and substituted 3-(1,2,3-triazol-l-yl)furazans have been synthesized.

Synthesis and antineoplastic properties of (1H-1,2,3-triazol-1-yl)furazans

A method of 3-amino-4-[5-aryl(heteroaryl)-1H-1,2,3-triazol-1-yl)]furazan synthesis was optimized. Condensation of these compounds with 2,5-dimethoxytetrahydrofuran resulted in a series of previously unknown 4-[5-aryl(heteroaryl)-1H-1,2,3-triazol-1-yl)]-3-(pyrrol-1-yl)furazans. All target compounds were evaluated for both antimitotic microtubule destabilizing effect in a phenotypic sea urchin embryo assay and cytotoxicity in a panel of 60 human cancer cell lines. Pyrrolyl derivatives of triazolylfurazans were determined as antiproliferative compounds. The most potent microtubule targeting compounds 7a and 7e are of interest for further trials as antineoplastic agents.

5-[4-amino(1,2,5)oxadiazolyl]-5H-[1,2,3]tri-azolo [4,5-c][1,2,5]oxadiazole from 4,4′-diamino-3,3′-azofurazane

Abstract4,4′-Diamino-3,3′-azofurazane undergoes intramolecular oxidative cyclization to give 5-[4-amino(1,2,5)oxadiazolyl]-5H-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazole upon heating with Pb(OAc)4 in chlorobenzene oro-dichlorobenzene or with thionyl chloride.

[Potentiation of activation of soluble guanylate cyclase by YC-1, NO-donors and increase of the synergistic effect of YC-1 on NO-dependent activation of the enzyme by 1,2,3-triazolyl-1,2,5-oxadiazole derivatives].

The influence of (1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazole derivatives: 4-amino-3-(5-methyl-4-ethoxycarbonyl-(1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazole (TF4CH3) and 4,4′-bis(5-methyl-4-ethoxycarbo-nyl-1H-1,2,3-triazol-1-yl)-3,3′-azo-1,2,5-oxadiazole (2TF4CH3) on stimulation of human platelet soluble guanylate cyclase by YC-1, NO donors (sodium nitroprusside, SNP, and spermine NONO) and on a synergistic increase of NO-dependent activation of the enzyme in the presence of YC-1 has been investigated. Both compounds increased guanylate cyclase activation by YC-1, potentiated guanylate cyclase stimulation by NO donors and increased the synergistic effect of YC-1 on the NO-dependent activation of soluble guanylate cyclase. The similarity in the properties of the examined 1,2,3-triazol-1-yl-1,2,5-oxadiazole derivatives with that of YC-1 and a possible mechanism underlying the recognized properties of compounds used are discussed.

Synthesis of 4,4′-bis(dichloroamino)- and 4,4′-bis(chloroamino)-3,3′-azofurazans, the first representatives of dichloroamino- and chloroaminofurazans

First representatives of dichloroamino- and chloroaminofurazans, viz., 4,4′-bis(dichloroamino)- and 4,4′-bis(chloroamino)-3,3′-azofurazans, were synthesized by the chlorination of 4,4′-diamino-3,3′-azofurazan with sodium hypochlorite in the CH2Cl2—H2O mixture.