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.

1,3-Bis(2-ethoxy-phen-yl)triazene.

Abstract: The title compound, C16H19N3O2, exhibits a trans geometry about the N=N double bond in the triazene unit in the solid state, and individual mol­ecules are close to planar with r.m.s. deviations from planarity of 0.065 A and 0.242 A for the two independent molecules in the asymmetric unit. Distinct inter­molecular N—H⋯N hydrogen bonds lead to the formation of dimers with an R22(8) graph-set motif. The steric demands of the eth­oxy groups in the ortho position prevent a coplanar arrangement of the two mol­ecules in the dimers and these instead consist of two inter­locked mol­ecules that are related by a non-crystallographic pseudo-twofold rotation axis. Weak C—H⋯π inter­actions between the CH groups and the aromatic phenyl rings also occur.

Triazene metabolism. II. Transportability and enzyme inhibitory characteristics of metabolites of antitumor dimethyltriazenes.

Abstract: A series of dimethyltriazenes (Ar∙N=N∙NMe2), monomethyltriazenes (Ar∙N=N∙NH∙Me), and triazene carbinolamines (Ar∙N=N∙NMe∙CH2OH) have been studied for their inhibitory effects on the enzyme, hog liver esterase (EC 3.1.1.1). p-Nitrophenyl acetate was used as the model substrate and the rate of hydrolysis was followed spectrophotometrically at 400 nm, the absorption maximum of the p-nitrophenylate ion. Only triazenes with an ester group in the aryl moiety exhibited significant inhibition. Preincubation of the enzyme with the monomethyltriazene (MeO2C∙C6H4∙N=N∙NHMe) or the methyloltriazene (MeO2C∙C6H4∙N=N∙NMe∙CH2OH) gave enhanced inhibition, which was not observed when the dimethyltriazene (MeO2C∙C6H4∙N=N∙NMe2) was preincubated with the enzyme. Inhibition of enzyme activity by the monomethyltriazene was shown to be essentially irreversible, whereas the model substrates, methyl benzoate and methyl p-aminobenzoate, gave reversible inhibition in the same assay. The inhibition by the N-methyloltriazene was only p...

Synthesis and Antiproliferative Activity of Triazenoindazoles and Triazenopyrazoles: A Comparative Study.

Abstract: Several triazenoindazoles and triazenopyrazoles were prepared transforming the appropriate aminoindazoles and aminopyrazoles in the corresponding diazonium salts which were reacted with dimethylamine, diethylamine and pyrrolidine. All the triazenes were tested for their antiproliferative activity against K562, HL60, L1210 and MCF7 cell lines. The biological data showed that the benzocondensation plays a positive role on the antiproliferative activity. The (1)H-NMR spectra showed that the rotational barrier around the N(2)-N(3) bond in the triazene group can be influenced both by the position of this group in the indazole nucleus and by the substitution pattern in the benzene moiety.

Solid phase synthesis of functionalized indazoles using triazenes – scope and limitations

Abstract: Indazoles are important heterocycles as they are a substantial part in many drugs. In this study, we present a modular synthesis of highly substituted indazoles via a strategy on solid supports. The heterocyclic nitrogen atoms originate from diazonium salts, being cleaved from triazene containing resins. The scope and limitations of this process are explored, considering especially the competitive occurrence of triazines and the cleavage of hydrolyzed and traceless side products.