Gas Chromatography-Mass Spectrometry Studies of Several Allyl-substituted 6-Azauracil Derivatives

http://www.revistadechimie.ro 964 It is established that analogues of natural nucleobases and nucleosides, containing nitrogen atoms have good antimetabolite [1, 2], antiviral, antibacterial [3, 4] antitumor and antimetastatic properties [5]. One of the first compounds obtained, exhibiting good antitumor and antimetabolite activity is 6-azauridine, an analogue of 6azauracil [2]. In recent years, a number of 6-azauracil analogues, N-substituted with alkyl groups containing a βheteroatom (O,S) [6] or vicinal olefinic double bond [7] have been reported as having antiviral properties. Beside some known compounds, we have reported the synthesis and characterization of new 5-substituted-6azauracils [8, 9]. However, N-substituted 6-azauracils bear increased similarity to natural nucleosides, exhibiting good potential for useful biological properties. The biological action and metabolism of 6-azauracil derivatives is fairly well known. This activity sterns from impairment of nucleic acid synthesis caused by the inhibition of orotic acid metabolism by phosphorilated 6azauridine [10]. The metabolites of 6-azauridine have been found to consist of 6-azauracil and phosphorilated 6azauridine, along with untransformed 6-azauridine [11]. In both 6-azauracil and 6-azauridine derivatives, the chemical bond strengths and lengths may have a wide range. This fact, coupled with the diverse chemistry of such triazine derivatives (for example see the rearrangement described in [12]), should allow, at least in theory, for a number of possible decomposition patterns of the triazine heterocycle under electron ionization. Gas Chromatography-Mass Spectrometry Studies of Several Allyl-substituted 6-Azauracil Derivatives