15837-08-8

Usage

Uses

Used in Pharmaceutical Research:
2,6-DIHYDROXY-3,9-DIMETHYLPURINE is used as a research compound for studying the molecular mechanisms of various biological processes. Its unique structure allows it to interact with specific targets, making it a valuable tool in the development of new drugs and therapies.
Used in Chemical Synthesis:
2,6-DIHYDROXY-3,9-DIMETHYLPURINE can be used as a starting material or intermediate in the synthesis of more complex organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, or materials science industries.
Used in Analytical Chemistry:
Due to its unique chemical properties, 2,6-DIHYDROXY-3,9-DIMETHYLPURINE can be employed as a reference compound or standard in analytical chemistry for the calibration of instruments or the development of new analytical methods.
Used in Biochemical Studies:
2,6-DIHYDROXY-3,9-DIMETHYLPURINE may be utilized in biochemical research to investigate the interactions between purine derivatives and various biomolecules, such as enzymes, receptors, or nucleic acids. This can provide insights into the role of these compounds in cellular processes and the development of novel therapeutic strategies.
Used in the Study of Ryanodine Receptors:
2,6-DIHYDROXY-3,9-DIMETHYLPURINE is used as a tool to study the in situ activation of ryanodine receptors (RY) in pancreatic β cells from ob/ob mice. This research can contribute to a better understanding of the molecular mechanisms underlying the regulation of these receptors and their role in cellular signaling pathways.

InChI:InChI=1/C7H8N4O2/c1-10-3-8-4-5(12)9-7(13)11(2)6(4)10/h3H,1-2H3,(H,9,12,13)

Upstream product

• 89465-16-7 1-methyl-6-methylamino-1H-pyrimidine-2,4-dione 
• 124770-89-4 C₃₀H₂₈N₄O₇ 
• 124770-90-7 (5-Benzyloxycarbonylaminocarbonyl-3-methyl-3H-imidazol-4-yl)-methyl-carbamic acid benzyl ester 
• 4022-89-3 1-Methyl-5-(methylamino)-1H-imidazole-4-carboxamide 
• 29052-39-9 1-methyl-6-(methylamino)-5-nitrosouracil 
• 31737-09-4 6-chloro-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione 
• 90049-59-5 5-formylamino-1-methyl-6-methylamino-1H-pyrimidine-2,4-dione 
• 82913-21-1 5-<(ethoxycarbonyl)methylamino>-1-methylimidazole-4-carboxamide 

Downstream Products

• 97722-94-6 3,7,9-trimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purinium; toluene-4-sulfonate 
• 55441-63-9 3,9-dimethyluric acid 

Relevant academic research and scientific papers

Purines XIV. [1]. Reactivity of 8-Bromo-3,9-dimethylxanthine Towards Some Nucleophilic Reagents

The reactivity of 8-bromo-3,9-dimethylxanthine (6) towards a variety of nucleophilic reagents has been investigated. Nucleophilic displacements take place easily with aliphatic mercaptans and aliphatic alcohols, whereas aliphatic amines required more severe conditions. Prolonged heating of 6 with amines causes a new type of rearrangement from 3,9- to 3,7-dimethylxanthines due to a 1,3-sigmatropic shift of the N(9)-methyl group.

3-METHYLXANTHOSINE: SYNTHESIS AND ACIDIC HYDROLYSIS OF THE GLYCOSYL BOND

An improved synthesis of 3,9-dimethylxanthine (2a) was achieved via the reaction of 1-methyl-5-(methylamino)-imidazole-4-carboxamide (3a) with EtOCOCl in acetate buffer (pH 5) followed by treatment with aqueous NaOH.This method was successfully applied to the synthesis of 3-methylxanthosine (2b), whose N-glycosidic bond proved to be remarkably sensitive to acidic hydrolysis: 2b underwent hydrolysis at a rate more than 1000 times faster than that of xanthosine (10) in 1.0N aqueous HCl at 25 deg C.Keywords: 3-methylxanthosine synthesis; 3,9-disubstituted xanthine; imidazolylcarbamic acid ester; base-catalyzed cyclization; amide carbamate cyclization; N-glycosidic bond hydrolysis; carbamate cis-trans isomerism; NMR; kinetic study

SYNTHESIS OF 3,9-DIALKYLGUANINES AND THEIR CONVERSION INTO 3-ALKYLWYES, MODELS FOR THE FLUORESCENT NUCLEOSIDES FROM PHENYLALANINE TRANSFER RIBONUCLEIC ACIDS

Synthesis of 3,9-dialkylguanines 5 has been accomplished by N-cyanation of 1-alkyl-5-(alkylamino)imidazole-4-carboxamides 3 followed by base-catalysed cyclisation.Cyclocondensation of 9-alkyl-3-methylguanines 5a, d, f with MeCOCH2Br gave 3-alkylwyes 6, model compounds of the most probable structure for wyosine from Torulopsis utilis tRNAPhe.

SYNTHESIS OF 3-METHYLXANTHOSINE

Treatment of 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-(methylamino)imidazole-4-carboxamide (VIb) with EtOCOCl followed by cyclization with 1 N NaOH gave 3-methylxanthosine (Va).The glycosidic bond of Va underwent acid hydrolysis at a rate more than 1000 times greater than that of xanthosine.