Tuberculosis is currently infecting more than 30% of the global population and accounts for 2 million deaths annually.      Adenosine kinase enzyme is a purine salvage enzyme that catalyzes adenosine phosphorylation to AMP and it has been shown that it leads to the conversion of 2-methyladnosine 1  to compounds with selective anti-mycobacterial activity.Encouraged by the promising anti-tubercular activity of 1,  our laboratory is seeking analogs with a different mode of action to overcome recently emerging resistant TB strains. In that direction, a series of carbocyclic analogs 2-5  were designed and synthesized for the assessment of their anti-tubercular activity.       The convergent synthetic procedures conducted for the construction of the target carbocyclic nucleosides include the employment of Grubbs metathesis, Luche's reduction and Mitsunobu coupling reactions.             Compounds 2  and 4  were tested and they did not show a significant activity.             This research has been supported by the Moletter Endowment for Drug Discovery.

Synthesis and antimycobacterial assessment of 2-methylaristeromycins

243rd National Meeting (2012)

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