Guanylhydrazones

Table 5.6 Urinary Excretion of Methylglyoxal-bis-Guanylhydrazone in Mammalian Species...

Oxidation of methyl ketone guanylhydrazones (686) with selenium dioxide affords the corresponding monosubstituted glyoxal derivatives (687) which cyclize to the 5-unsubstituted 3-amino-1,2,4-triazines (473) (78HC(33)189, p.360). We have already noted the cyclization of bis(alkylidene)- or bis(arylidene)-acetone guanylhydrazones (475) in the synthesis of 6-(vinyl-substituted) 3-amino-1,2,4-triazines (477) (Section 2.19.4.1.1). 

LA 150). A similar report of triazocirte formation by cyclization of phe-nacyl bromide guanylhydrazone hydrobromide with base (56AG374 57-LA50) was also shown to be incorrect, the product being instead an imidotriazine (68TL789). 

Although some guanylhydrazone-thiosemicarbazones showed high antitubercular activity, 176 did not. 6-Acyl- and 6-aroyl-5i7-1 -pyrin-dine-5,7(6//)-diones also react with hydrazine.112... 

N-Vinylpyrrole semicarbazones 158a-c, thiosemicarbazones 159a-c and guanylhydrazones 160a-c were obtained in 68-91% yields from N-vinylpyrrole-2-carbaldehydes 157a-c with semicarbazide, thiosemi-carbazide and aminoguanidine (Equation (48)) (08CHE1117). 

Stanek, J., Caravatti, G., Capraro, H.-G., Furet, P, Mett, H., Schneider, P, Regenass, U. S-Adenosylmethionine decarboxylase inhibitors new aryl and heteroaryl analogues of methylglyoxal bis(guanylhydrazone). J. Med. Chem. 1993, 36, 46-54. 

Periodate can be determined by its redox reaction with o-dianisidine [35], benzhydrazide [36], or 2,2 -azinodi(3-ethylbenzothiazolesulphonic acid) [37] and phthalimide-bisthiosemicarbazone (e = 2.8-10 ) [38]. Cyclohexane-1,3-dione bis-thiosemicarbazone [39], 3,4-dihydroxybenzaldehyde guanylhydrazone [40], salicylaldehyde guanylhydrazone [41], and amyloride hydrochloride [42] allow IO4 to be determined in the presence of 103". 

Hydroxylamine (NH2OH) can be determined by its colour reaction with di(2-pyridyl) ketone guanylhydrazone [113]. It can also be determined in an indirect method by its reaction with biacetyl to give dimethylglyoxime, which then reacts with Ni(II) [114]. The FIA technique has been applied in the determination of NH2OH with the use of ferrozine [115]. A review has been given of methods used for the determination of hydrazine [116]. 

In the aldoxime, the aldehyde guanylhydrazone and vinyl-quinoline compar-isons°9 of Coli-Staph. activity in vitro, changing 5-nitro- to -methylsul-fonyl- furyl produced to 100-fold decreases in activity, in contrast to the same variation on chloranrohenicol. 

The reaction mechanism of formazan formation has been studied by many researchers. The fundamental work of Busch and his coworkers and the studies by Hiinig and Boes, and by Hauptmann and Perissd, merit special mention. A host of other authors have endeavored to widen the sphere of application of the formazan reaction, and have extended it successfully to the 4,4-iV-diarylsemicarbazonesi and guanylhydrazones, -i respectively. 

TABLE 5.6 Urinary excretion of methylglyoxal-bis-guanylhydrazone in mammalian species... 

Karfunkel, H. R., Z. J. Wu, A. Burkhard, G. Rihs, D. Sinnreich, H. M. Buerger, and J. Stanek. 1996. Crystal packing calculations and Rietveld refinement in elucidating the crystal structures of two modifications of 4-amidoindanone guanylhydrazone. Acta Cryst. B52 555-561. 

VIII r,5-Bis-(5-nitro-2-furyl)penta-i,4-dien-3-one guanylhydrazone hydrochloride (panazone). 

Beilstein Handbook Reference) 1,5-Bis(5-nitro-2-furanyl)-1,4-pentadien-3-one, (aminoimino-methyl)hydrazone sym-Bis(6-nitro-2-turfurylidene) acet-one guanylhydrazone Bis(2-(5-nitro-... 

McCullough, J.L., Peckham, P, Klein, J., Weinstein, G.D., and Jenkins, J.J. (1985). Regulation of epidermal proliferation in mouse epidermis by combination of difluoromethyl ornithine (DEMO) and methylglyoxal bis(guanylhydrazone) (MGBG), J. Invest. Dermatol, 85 518-521. 

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