Abstract
Cu(I) catalyzed alkyne-azide cycloaddition reaction was employed to synthesize a series of anthracene-based human thymidylate synthase (hTS) inhibitor analogues. The triazolo-anthracene derivatives were characterized by ESI-MS/MS and a novel rearrangement reaction in ESI-MS/MS was observed. The mechanism is proposed whereby the protonated triazolo-anthracene derivative forms a carbocation, and then the carbocation electrophilically attacks an anthracene moiety resulting in formation of a rearrangement ion. Moreover, the carbocation prefers to attack the γ position rather than the α or β position of the anthracene moiety by an electrophilic substitution mechanism.
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Published online December 3, 2009
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Chen, Y., Le Droumaguet, C., Li, K. et al. A novel rearrangement of fluorescent human thymidylate synthase inhibitor analogues in ESI tandem mass spectrometry. J Am Soc Mass Spectrom 21, 403–410 (2010). https://doi.org/10.1016/j.jasms.2009.11.004
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DOI: https://doi.org/10.1016/j.jasms.2009.11.004