Heterocyclic N-oxides have proven to be an interesting class of antitumor agents that selectively kill the hypoxic cells found in solid tumors. Tirapazamine, the lead compound of this class that has undergone extensive study, exhibits hypoxia-selective activity via an intracellular one-electron reduction mechanism followed by a deoxygenative mechanism to form key DNA damaging intermediates, which include the formation of a hydroxyl radical. Myxin (1-hydroxy-6- methoxyphenazine- N5, N10-dioxide), another compound that belongs to the heterocyclic N-oxide class has been shown to cause bioreductively activated, radical-mediated DNA strand cleavage under both aerobic and anaerobic conditions via a deoxygenative mechanism analogous to that characterized for tirapazamine, thus making it a potential antitumor as well as antibacterial candidate. In order to improve both the solubility of myxin as well as its potential bioactive properties, different glycosylated analogues have been synthesized. References1.) Chodury, G.; Sarkar, U.; Pullen, S.; Wilson, W.R.; Rajapakse, A.; Fuchs-Knotts, T.; Gates, K.S. Chem. Res. Toxicol. 2012, 25, 197-206.

Synthesis of glycosylated myxin analogs

245th National Meeting (2013)

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