5227-68-9

Usage

Uses

Used in Biomarker Research:
Guanine 7-oxide is used as a biomarker for oxidative stress due to its formation through the oxidation of guanine. It helps in understanding the role of oxidative stress in various diseases and conditions.
Used in Cancer Research:
Guanine 7-oxide is used as a research tool in cancer studies for its mutagenic and carcinogenic properties. It aids in investigating the development of certain types of cancer and its potential implications in disease progression.
Used in Genetic Research:
Guanine 7-oxide is used as a precursor to 8-oxo-7,8-dihydroguanine, a highly mutagenic lesion in DNA. It is employed in genetic research to study the mechanisms of genetic mutations and their consequences on cellular functions and disease development.
Used in Pharmaceutical Development:
Guanine 7-oxide may be used as a target for the development of drugs or therapies aimed at reducing oxidative stress, preventing mutations, or treating cancer. Research into its biological effects and potential health implications is ongoing to explore its potential applications in the pharmaceutical industry.

InChI:InChI=1/C5H5N5O2/c6-5-8-3-2(4(11)9-5)10(12)1-7-3/h1H,(H4,6,7,8,9,11)

Upstream product

• 117233-74-6 2-amino-6-<(3,4-methylenedioxybenzyl)(2-oxo-2-phenylethyl)amino>-5-nitro-4(3H)-pyrimidinone 
• 117233-76-8 2-amino-6-<(3,4-dimethoxybenzyl)(2-oxo-2-phenylethyl)amino>-5-nitro-4(3H)-pyrimidinone 
• 112698-43-8 2-amino-6-<(4-methoxybenzyl)(2-oxo-2-phenylethyl)amino>-5-nitro-4(3H)-pyrimidinone 
• 117233-73-5 9-(3,4-methylenedioxybenzyl)guanine 7-oxide 
• 117233-72-4 9-(3,4-dimethoxybenzyl)guanine 7-oxide 
• 112698-48-3 9-(4-methoxybenzyl)guanine 7-oxide 

Relevant academic research and scientific papers

Purines. L. Synthesis and antileukemic activity of the antibiotic guanine 7-oxide and its 9-substituted derivatives

A full account is given of the first chemical synthesis of the antitumor antibiotic guanine 7-oxide (5) and its 9-substituted derivatives (24a-k and 26). Coupling of appropriate primary amines (17a-e, g-k) with phenacyl bromide (16) produced, after treatment with HCl, the corresponding N-substituted phenacylamine hydrochlorides (18a-e, g-k). A similar phenacylation of 4-amino-1-butanol (21) failed to give the desired compound 18f, so that 21 was heated with 2-bromomethyl-2-phenyl-1,3-dioxolane (20) at 150-155°C for 3 h to furnish, after treatment with HCl, the amino ketal hydrochloride 22 in 40% yield. Deketalization of 22 with hot 2 N aqueous HCl afforded 18f in 96% yield. Condensations of the free bases, generated in situ from the hydrochlorides 18a-l and 1 N aqueous NaOH, with the chloropyrimidinone 6 were effected in aqueous EtOH at the boiling point for 20 minor at 25-30°C for 3-24 h, giving the 6-phenacylamino-4-pyrimidinones 19a-l in 54-90% yields. On treatment with 2 N aqueous NaOH at room temperature for 10-60 min, the nitropyrimidinones 19a-k cyclized to provide the 9-substituted guanine 7-oxides 24a-k in 61-98% yields. A similar alkali-treatment of 19 l failed to yield guanine 7-oxide (5). However, removal of the 9-(arylmethyl) group from 24i-k was effected with conc. H2SO4 at room temperature for 1-3 h in the presence of toluene, producing the target N-oxide 5 in 56-89% yields. In the in vitro bioassay of antileukemic activity against murine L5178Y cells, none of the 9-substituted guanine 7-oxides (24a-k and 26) was more effective than the parent, natural N-oxide 5. Within this series, however, the benzyl analogues 24g-k withor without alkoxy functions were more cytotoxic, with IC50's of 13.0-48.0 μg/ml, than the alkyl analogues 24a-f.

SYNTHESIS OF GUANIN 7-OXIDE, AN ANTITUMOR ANTIBIOTIC FROM STREPTOMYCES SPECIES

The first synthesis of the antitumor antibiotic guanine 7-oxide (VI) has been achived via a 4-step route starting from phenacyl bromide (I) and the nitropyrimidone III and proceeding through the intermediates IVe and Ve.