13231-00-0

Usage

Uses

Used in Pharmaceutical Industry:
7,9-dihydro-1H-purine-6,8-dione is used as a bronchodilator for the treatment of respiratory disorders such as asthma and chronic obstructive pulmonary disease (COPD). It operates by relaxing the smooth muscles that line the airways, thereby enhancing breathing efficiency.
Used in Stimulant Applications:
As a stimulant, 7,9-dihydro-1H-purine-6,8-dione is utilized to increase alertness and reduce fatigue by stimulating the central nervous system, making it beneficial for individuals requiring enhanced cognitive performance or physical endurance.
Used in Diuretic Applications:
7,9-dihydro-1H-purine-6,8-dione also serves as a mild diuretic, promoting the excretion of excess water and salts from the body, which can be advantageous in managing conditions related to fluid retention or high blood pressure.

InChI:InChI=1/C5H4N4O2/c10-4-2-3(6-1-7-4)9-5(11)8-2/h1H,(H3,6,7,8,9,10,11)

Upstream product

• 75-44-5 phosgene 
• 1672-50-0 5,6-diamino-4(3H)-pyrimidinone 
• 57-13-6 urea 
• 52502-66-6 5,6-diamino-3H-pyrimidin-4-one; sulfate 
• 21149-25-7 adenine 7-oxide 
• 68-94-0 hypoxanthine 
• 118974-81-5 hypoxanthine 7-N-oxide 
• 21149-25-7 adenine 7-oxide 
• 118974-80-4 6-<(4-methoxybenzyl)(2-oxo-2-phenylethyl)amino>-5-nitro-4(3H)-pyrimidinone 
• 118974-82-6 9-(4-methoxybenzyl)hypoxanthine 7-N-oxide 
• 155854-86-7 3-Benzyl-7-oxy-3H-purin-6-ylamine 
• 7280-81-1 3-benzyladenine 
• 66224-66-6 adenine 

Downstream Products

• 28128-33-8 7(9)H-purine-6,8-diyldiamine 
• 28128-28-1 8-chloroadenine 
• 6974-66-9 8-chloro-1,7-dihydro-purine-6-thione 
• 22712-29-4 8-chlorohypoxanthine 
• 37527-48-3 6-chloro-7H-purin-8(9H)-one 
• 28128-32-7 8-Methoxyadenin 
• 19916-15-5 6,8-dichloro-7(9)H-purine 
• 20917-46-8 6-Thioxopurin-8-on 

Relevant academic research and scientific papers

Purines. LXVI. Adenine 7-oxide: Its synthesis, chemical properties, and X-ray molecular structure

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.

SYNTHESIS OF ADENINE 7-OXIDE FROM ADENINE: UTILIZATION OF A BENZYL GROUP AS A CONTROL SYNTHON AT THE 3-POSITION

The first unequivocal synthetic route to adenine 7-oxide (7) has been established.The route started with peroxycarboxylic acid oxidation of 3-benzyladenine (5), readily obtainable from adenine (2) by benzylation, 8nd proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (6).

Purines. LI. Synthesis and biological activity of hypoxanthine 7-N-oxide and related compounds

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.

SYNTHESIS OF HYPOXANTHINE 7-OXIDE, A NEW N-OXIDE AT THE 6-OXOPURINE LEVEL

Hypoxanthine 7-oxide (IV) has been synthesized for the first time from 6-chloro-5-nitro-4(3H)-pyrimidinone (I) through the intermediates II and V; catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and isomerization under acidic conditions of IV supported the correctness of the assigned structure.

Regioselectivite de la reaction des radicaux hydroxyle et hydroxy-2 propyle-2 avec l'hypoxanthine

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.