1.2.4- Triazino indoles

A. Heterocyclo-triazino-indoles 1. Imidazo-triazino-indoles... 

Garcia, E., Lopezdecerain, A., Martinez Merino, V. and Monge, A. (1992). Quantitative Structure Mutagenic Activity Relationships of Triazino Indole Derivatives. Mut.Res., 268,1-9. 

Thlosemicarbazones - No clinical experiments utilizing isatin thiosemicarbazones in poxvirus infections were reported during this period. The finding that isatin thiosemicarbazones active against poxvirus also inhibit the multiplication of certain strains of rhinovirus led to the finding that 2-methyl-4 5-tnethyl-5H-as-triazino- indol-5-yl)amin5 -2-... 

Treatment of l-ethylideneamino-3-methylindole 95 with p-toluene sulfonic acid in boiling benzene gave l,2-dihydro[l,2,4]triazino[l,6-a]indole 96 (75CPB2891). The reaction was said to be due to an initial formation of a Diels-Alder-type adduct followed by the liberation of 3-methylindole. Compound % was oxidized either on exposure to air or by the action of chloranil to give 97 (Scheme 24). 

Much work is still appearing on the [l,2,4]triazino[5,6-b]indole ring system since its first synthesis, due to its varied biological properties. Moreover, it has been used as a carrier for diverse functional groups suitable for the development of several chemotherapeutic agents. In addi-... 

It has been said that the above procedure cannot be applied to the synthesis of the corresponding nitro derivative, 8-nitro[l,2,4]triazino[5,6-b]indole-3-thione. Thus, heating 5-nitroisatin-3-thiosemicarbazone in aqueous potassium carbonate gave after acidification a mixture of oxotria-zinethione 137 and 5-nitroindazole 3-carboxylic acid (90ZOR1327). 

The synthesis of 2-aryl-2,3-dihydro[l,2,4]triazino[5,6-6]indol-3-ones 151 has been carried out (80MI2) by the cyclization of arylazoindolyl... 

Condensation of 165 with ethoxymethylenemalononitrile gave 171, and with ethyl ethoxymethylenecyanoacetate or methyl bis(methylmercapto)-methylene cyanoacetate it yielded 172 (80AP108). The reaction of 172 with urea, thiourea, and benzyl nitrile afforded 173 (91PHA98). Treatment of hydrazino derivatives 165 with alkyl, aryl, or aralkyl isothiocyanates yielded (86JHC1731) 3-(/V-substituted-thiocarbamoyl)-hydrazino[l,2,4]triazino[5,6-b]indoles which have been evaluated for in vitro antimicrobial activity (Scheme 36). 

Aroylation of 3-arylhydrazonoisatin with aroyl chlorides gave 1043, which cyclized with ammonium acetate to give [1,2,4]triazino[5,6-A>]indole 1044 (92MI1). Derivatives of 1045 were prepared (92MI1). Cyclocondensation of 5-ethyl-3-hydrazino-5/f[l,2,4]triazino[5,6-b]indole 165 with succinic anhydride in acetic acid gave pyridazinedione derivative 1046 (90MI7) (Scheme 197). 

A derivative of 163, 3-(2-morpholinoethylthio)[l,2,4]triazino[5,6-fo]indole dihydrochloride, is used as a thrombolytic (91URP1672373). Derivatives of the pyrazolo[5,l-c][l, 2,4]tria-zines were used as a constituent of silver halide color photographic supported material, which showed good color reproducibility [91JAP(K)03/291649]. The protective action of [l,2,4]triazino[4,3-a]benzimidazoles as corrosion inhibitors was studied (91MI8). 

The imidazo[ 1,2-b][l,2,4]triazino[5,6-6]indoles 597 were prepared by reacting 3-amino[l, 2,4]triazino[5,6-6]indole 592 with a-bromoketones 596. The structure was confirmed by the identity with the product of a reaction between isatin 599 or 2-phenylimino-3-oxoindole 600 and 1,2-diamino-4,5-diphenylimidazole 598 (82ZOR1272). Similarly, a cyclocondensation of 1,2-diamino-4-arylimidazoles with isatin and N-methylisatin was carried out (82KGS242). 

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