1-Aryl-3-(hydroxymethyl)-3-alkyltriazenes [ArN = NN(CH3)CH2OH] have been synthesized by diazonium coupling to the carbinolamine (RNHCH2OH), generated in situ from the alkylamine and
formaldehyde mixtures. The (hydroxymethyl)triazene structure has been confirmed by IR, NMR, and mass spectral analysis and also by the preparation of a crystalline
benzoate derivative. The mass spectra of the (hydroxymethyl)
triazenes suggest that they fragment by loss of
formaldehyde to give the methyltriazene, which is also the product of hydrolysis in
solution. The degradation of the (hydroxymethyl)
triazenes in
solution has been followed by UV spectroscopy and by HPLC analysis, and the half-lives were determined under a variety of conditions. The half-lives of the corresponding methyl- and (hydroxymethyl)
triazenes are very similar. Both methyl- and (hydroxymethyl)
triazenes decompose on
silica plates during TLC analysis to give products consistent with known diazo-migration reactions. The (hydroxymethyl)
triazenes have pronounced antitumor activity against the TLX5
tumor in vivo; in vivo-in vitro bioassay experiments suggest that the (hydroxymethyl)
triazenes exert their in vivo antitumor activity via the degradation product, the alkyltriazene.