70346-62-2Relevant academic research and scientific papers
Studies of the mode of action of antitumor triazenes and triazines. 6. 1-Aryl-3-(hydroxymethyl)-3-methyltriazenes: Synthesis, chemistry, and antitumor properties
Vaughan,Tang,Llanos,Horton,Simmonds,Hickman,Stevens
, p. 357 - 363 (2007/10/02)
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.
OPEN-CHAIN NITROGEN COMPOUNDS. PART V. HYDROXYMETHYLTRIAZENES: SYNTHESIS OF SOME NEW ALKYL HOMOLOGUES OF THE ANTI-TUMOUR 3-METHYL-3-HYDROXYMETHYLTRIAZENES AND PREPARATION OF THE DERIVED ACETOXYMETHYL-, BENZOYLOXYMETHYL-, AND METHOXYMETHYLTRIAZENES
Hemens, Chantal M.,Manning, Hartford W.,Vaughan, Keith,LaFrance, Ronald,Tang, York
, p. 741 - 748 (2007/10/02)
The synthesis of some new 1-aryl-3-alkyl-3-hydroxymethyltriazenes is described.The method of coupling a diazonium salt with an alkylamine/formaldehyde mixture has been extended to (a) some diazonium ions with para substituents other than -M groups, (b) those with substituents in ortho position, and (c) to homologous alkylamines (e.g. ethylamine, propylamine, etc.).Hydroxymethyltriazenes can also be prepared by the reaction of a 1-aryl-3-methyltriazene with formaldehyde.Several new derivatives of hydroxymethyl function have been prepared.Reaction with acetic anhydride or benzoyl chloride in pyridine affords respectively the acetoxymethyl- and benzoyloxymethyl-triazenes; the acetates and benzoates react readily with methanol to give the novel methoxymethyltriazenes.This is the first report of a series of dialkyltriazenes with an ether linkage in the α position. An ether of this type has also been obtained directly from the diazonium fluoroborate salt by coupling with a mixture of benzylamine and formaldehyde in ethanolic solution.
