Topic
Triazene
About: Triazene is a research topic. Over the lifetime, 759 publications have been published within this topic receiving 8714 citations. The topic is also known as: Triazene cleavage & 1-triazene.
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TL;DR: The triazene protected amine is compatible with oxidative and reductive conditions as well as with strong bases (LDA, tert-butyllithium) and alkylating reagents as discussed by the authors.
37 citations
TL;DR: Results suggest that the chloroethyl group is the favored initial site of metabolism of 1-(2-chloroethyl)-3-methyl-3-(methylcarbamoyl)triazene and carbamoyltriazene metabolites.
Abstract: (Methylcarbamoyl)triazenes have been shown to be effective cancer chemotherapeutic agents in a number of biological systems. Because of their chemical stability, it is likely that their activity in vivo is the result of a metabolic activation process. Previous studies have shown that 1-(2-chloroethyl)-3-methyl-3-(methylcarbamoyl)triazene (CMM) and 1-(2-chloroethyl)-3-benzyl-3-(methylcarbamoyl)triazene (CBzM) are metabolized by rat liver microsomes in the presence of NADPH to yield the ((hydroxymethyl)carbamoyl)triazene analogs of the parent compounds. The present studies show that both compounds are also oxidized at the chloroethyl substituent to yield chloroacetaldehyde and a substituted urea. In the case of CBzM metabolism, 47% of the metabolized parent compound was recovered as benzylmethylurea, 8% was recovered as benzylurea, and 26% was recovered as the ((hydroxymethyl)carbamoyl)-triazene and carbamoyltriazene metabolites. These results suggest that the chloroethyl group is the favored initial site of metabolism. In reaction mixtures containing initial concentrations of 300 microM CBzM, 78 microM chloroacetaldehyde was produced, as compared to 58 microM chloroacetaldehyde produced from the metabolism of 300 microM CMM. The formation of chloroacetaldehyde, a known mutagenic DNA alkylating agent, may explain the biological activity of these compounds.
36 citations
TL;DR: Aryl triazenes, a source of aryl radicals, were coupled with heteroarenes via C–H functionalization to produce heterobiaryls in moderate to good yields and both electron donating and withdrawing substituents in the triazene moieties were tolerated.
Abstract: Aryl triazenes, a source of aryl radicals, were coupled with heteroarenes via C–H functionalization to produce heterobiaryls in moderate to good yields. Couplings proceeded under an open atmosphere at ambient temperature for 3–24 h. Best results were obtained with electron-deficient heteroarenes, while both electron donating and withdrawing substituents in the triazene moieties were tolerated.
35 citations
TL;DR: In this paper, the reaction of [1,3-di(2-methoxy)benzene]triazene, [ HL], with Hg(CH 3 COO) 2 and HgL 2 in methanol as solvent, resulted in the formation of [HgL 1 ] (1 ) and [hgL(SCN)] (2 ), respectively.
34 citations
TL;DR: The site of attachment to beta-galactosidase of the active site-directed inhibitor, beta-D-Galactopyranosylmethyl p-nitrophenyl triazene, was determined and the radioactive label was found to be covalently bound to methionine residue 500.
34 citations