Monoalkyltriazenes

Dopamine- and tyramine-based derivatives of triazenes: Activation by tyrosinase and implications for prodrug design

“…Among all the chemotherapeutic agents tested against this malignancy, DTIC is the most active single agent and thus considered the reference drug [10,11]. Related 1-aryl-3,3-dimethyltriazenes, 3, (see Scheme 1) are also documented as anticancer drugs, but with reduced selectivity for tumour cells [12,13].…”

Effect of Lonidamine on Systemic Therapy of DB-1 Human Melanoma Xenografts with Temozolomide

“…The mechanism of acid-catalyzed alkylation of guanine by TMZ has not been clearly delineated. It appears, however, to involve conversion of TMZ to MTIC, which then is converted to diazomethane and the methyldiazonium cation (18,60). The methyldiazonium ion is a potent electrophilic alkylating agent that binds in the major groove of DNA interacting preferentially with runs of multiple guanine residues and alkylating this base at O 6 or N 7 .…”

Open-chain nitrogen compounds. Part XII. Methanolysis of 3-alkyl-3,4-dihydro-1,2,3-benzotriazin-4-ols: evidence for ring-chain tautomerism with the cytotoxic monoalkyltriazenes

“…A mechanism of action study of this novel and potent anti-tumor agent has shown (3) that cytotoxicity is exerted by a metabonate of the drug and that the most likely species responsible for cytotoxicity is the monochloroethyltriazenoimidazole ("MCTIC") (2). Thus mitozolomide acts as a "pro-drug," without the need for metabolic activation, for the cytotoxic monoalkyltriazene, in contrast to the anti-tumor dimethyltriazenes, which require metabolic N-demethylation to generate the cytotoxic monomethyltriazene (4).…”