Synthesis of guanine 7-oxide, an antitumor antibiotic from species

Acremolin from Acremonium strictum is N2,3-Etheno-2′-isopropyl-1-methylguanine, not a 1H-Azirine. Synthesis and Structural Revision

“…16,17 Attempted removal of the PMB group of 10 by hydrogenolysis (H 2 , Pd-C, MeOH, 1 atm, 16 h) returned only starting material. Friedel-Crafts type transbenzylation, under the conditions reported by Fujii and coworkers (90% aq H 2 SO 4 , toluene, 40 °C), 18 smoothly delivered samples of 5a of high purity, albeit in low yield (39%). 19 Gratifyingly, 5a was obtained in good yield (76%) by simple treatment of 10 with neat CF 3 CO 2 H (40–80 °C).f…”

Metalated 1‐(p‐Methoxybenzyl)pyrazole: A Structural Chameleon

“…The p-methoxybenzyl ("PMB") entity is a protective group which can be easily removed not only by hydrogenolysis [18,19] (as benzyl itself), but also by oxidation [19,20] or by cleavage under acidic conditions. [21,22] …”

Oxidation chemistry of adenine N1-oxide, a potent oncogenic agent, at a pyrolytic graphite electrode

“…[1][2][3] The presence of the N-oxide group in purines has been found to induce antibiotic activity. 4 Several purine N-oxides have been reviewed in relation to their oncogenic 5 and antitumor properties. 6 Heterocyclic aromatic N-oxides such as quinoxaline dioxides have been used in the treatment of tuberculosis, as anticancer agents and also as bioreductive drugs for the treatment of solid tumors.…”