Triazenes are well known for their broad range of biological and therapeutic activities. For example, 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide (DTIC) is an antitumor agent clinically used in the therapy of disseminated sarcoma of man, etc.[1]. The 1,3-bis(4-amidiniumphenyl)triazene berenil has veterinary application as an antitrypanosomal agent, and has cytotoxic and anti-viral properties [2]. 3-Glycopyranosylmethyl-1-aryltriazenes, e.g. a, are active-site-directed irreversible inhibitors of diverse glycosidases [3 -12]. The enzyme inhibition results from an irreversible alkylation of a specific methionine of the protein chain by a cation b [3,4].Abstract. O-Unprotected glycosyltriazenes are prepared for the first time by coupling of 1-anthraquinone-1-diazonium hydrogensulfate with β-glycopyranosylamines to afford 1-(anthraquinone-1-yl)-3-(β-glycopyranosyl)triazenes 3a -h. Acetylation of compounds 3 furnished the O-acetates 4a -g. The stability of triazenes 3 results from fixation of the NH [17]. However, attempts to prepare O-unprotected glycosyltriazenes so far met with failure [16,18,19]. Thus, no glucosyltriazenes were produced by reaction of N-(p-tolyl)-D-glucopyranosylamine with 4-methyl-or 2,5-dichlorobenzenediazonium chloride [16]. O-Unprotected glycosyltriazenes would be of interest, inter alia, because of possible pharmaceutic activities.Our interest in glycosyltriazenes arose from the observation that certain 1,3-disubstituted triazenes c can be oxidized with tert-butyl hypochlorite to N-chlorotriazenes d, which with Lewis acids such as antimony pentachloride afford 1,3-diaza-2-azoniaallene salts e as reactive intermediates, which undergo 1,3-dipolar cyproton in an intramolecular hydrogen bond to one of the anthraquinone carbonyl oxgen atoms. Treatment of triazenes 4 with tert-butyl hypochlorite afforded acetoglycosyl chlorides 6 and 1-azidoanthraquinone 7. With acetic acid the triazene 4a formed tetra-O-acetyl-D-xylopyranose 9 together with 1-aminoanthraquinone 10.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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