13231-00-0Relevant articles and documents
Purine N-oxides. 23. Rearrangements of purine 3-N-oxides on acylation and methylation.
Woelcke,Pfleiderer,Delia,Brown
, p. 981 - 983 (1969)
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Purines. LXVI. Adenine 7-oxide: Its synthesis, chemical properties, and X-ray molecular structure
Fujii,Ogawa,Saito,Kobayashi,Itaya,Date,Okamura
, p. 53 - 62 (2007/10/02)
A detailed account is given of the first unequivocal synthesis of adenine 7-oxide (8). The synthesis started with peroxycarboxylic acid oxidation of 3-benzyladenine (6), readily obtainable from adenine (1) by benzylation, and proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (7). The location of the oxygen function in 7 and 8 was confirmed by their chemical reactions including deamination and methylation and by X-ray crystallographic analysis. A UV spectroscopic approach suggested that the neutral species of 8 exists in H2O as an equilibrated mixture of the NO-oxide (8) and N(7)-OH (21) tautomers. Treatment of 6 with 30% aqueous H2O2 in MeOH in the presence of MeCN and KHCO3 at 30°C produced the N(7)-oxide 7 and 7-acetamido-3-benzyladenine (15) in 12% and 1% yields, respectively.
Purines. LI. Synthesis and biological activity of hypoxanthine 7-N-oxide and related compounds
Ogawa,Nishii,Nohara,Saito,Itaya,Fujii
, p. 612 - 616 (2007/10/02)
A detailed account is given of the first chemical synthesis of hypoxanthine 7-N-oxide (5), which started from coupling of 6-chloro-5-nitro-4(3H)-pyrimidinone (7) with N-(4-methoxybenzyl)phenacylamine, generated in situ from the hydrochloride (8), and proceeded through cyclization of the resulting phenacylamino pyrimidinone (9) and removal of the 4-methoxybenzyl group. The results of catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and rearrangement under acidic conditions of 5 supported the correctness of the assigned structure. An ultraviolet spectroscopic approach suggested that the neutral species of 5 exists in H2O mainly as the N(7)-OH tautomer (21). In the in vitro bioassay of antileukemic activity against murine L5178Y cells, 5 was weakly cytotoxic, with IC50 of 100 μg/ml. It did not show any antimicrobial activity even at 1000 μg/ml. None of the 9-(4-methoxybenzyl) (11) and O-methyl (12, 13, and 14) derivatives was found to be antileukemic or antimicrobial.
Regioselectivite de la reaction des radicaux hydroxyle et hydroxy-2 propyle-2 avec l'hypoxanthine
Zylber, Jean,Zylber, Nicole,Lefort, Daniel,Ferradini, Christiane,Hickel, Bernard
, p. 283 - 287 (2007/10/02)
The reactivity of OH and (CH3)2COH radicals with hypoxanthine was studied under comparable γ-irradiation conditions.A difference in regioselectivity of attack by the elelctrophilic OH radical and the nucleophilic (CH3)2COH radical is observed, the latter leading in 70percent yield to a C-8 substituted product.The rate constants of the addition of the radical to hypoxanthine were determined by pulse radiolysis to be k = 1.4E8 M-1 s-1 in acid medium, and in neutral medium k = 7E5 M-1 s-1.The much more reactivee OH radical leads essentially to degradation products arising, inter alia, from attack on C-2 (resulting in the formation of xanthine, which disappears rapidly), while attack at C-8, approximately three times less rapid, leads to the 6,8-diketo purine, which does not undergo further reactions and thus accumulates in the medium.
