4566-77-2Relevant articles and documents
N6-Substituent Effect on the Photooxidation of 2',3'-O-Isopropylideneadenosines with a Pyrimidopteridinetetraone N-Oxide. Chemical Evidence for the Generation and Reactivity of Adenosyl Cation Radicals
Sako, Magoichi,Makino, Toru,Kitada, Yukio,Hirota, Kosaku,Maki, Yoshifumi
, p. 1801 - 1806 (2007/10/02)
A comparative study on the photooxidation of 2',3'-O-isopropylideneadenosine 1a and its N6-benzoyl, N-6-monomethyl, and N6,N6-dimethyl derivatives, 1b-d, with a pyrimidopteridinetetraone N-oxide (PPO) was carried out.The ease of photooxidative consumption of the adenosines by the PPO is in the order 1d > 1c > 1a > 1b, which is parallel to their oxidation-peak potentials.Although substrates 1a and 1b underwent oxidative intramolecular cyclisation to the corresponding 5'-O,8-cycloadenosines, 2a and 2b, even in low yield, substrates 1c and 1d were exclusively oxidised at the N6-methyl group to give the corresponding N6-formyl derivatives, 3 and 4, together with minor amounts of demethylated products, 1a and 1c.The present observations provide chemical evidence for the generation and reactivity of adenosyl cation radicals.
Studies on compounds related to antitumor agents. Synthesis of 8-substituted N6,N6-dimethyladenosine derivatives
Kato,Arakawa,Ogawa,Suzumura
, p. 3635 - 3643 (2007/10/02)
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