6505-01-7

Usage

Uses

Used in Pharmaceutical Applications:
6-Phenylpurine is used as a therapeutic agent for the treatment of respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD). By antagonizing adenosine receptors, it may help in reducing inflammation and bronchoconstriction, thereby alleviating symptoms associated with these conditions.
Used in Cardiology:
In the field of cardiology, 6-Phenylpurine is utilized as a potential treatment for cardiac arrhythmias. Its adenosine receptor blocking capability can be beneficial in managing abnormal heart rhythms by influencing the electrical activity of the heart.
Used in Scientific Research:
6-Phenylpurine serves as a valuable research tool in the study of adenosine receptor function and pharmacology. It aids researchers in understanding the mechanisms of adenosine action and in developing new drugs targeting adenosine receptors for various therapeutic purposes.
Each application leverages the unique ability of 6-Phenylpurine to modulate adenosine receptor activity, offering potential benefits across different medical disciplines.

InChI:InChI=1/C11H8N4/c1-2-4-8(5-3-1)9-10-11(14-6-12-9)15-7-13-10/h1-7H,(H,12,13,14,15)

Upstream product

• 960-16-7 tributylphenylstannane 
• 87-42-3 6-chloropurine 
• 50-66-8 6-methylthiopurine 
• 175787-78-7 6-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 7306-68-5 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 98-80-6 phenylboronic acid 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 328378-37-6 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-phenylpurine 
• 1416131-75-3 C₄₂H₄₄Cl₂Ir₂N₈ 
• 84765-98-0 6-phenyl-9-(β-D-ribofuranosyl)-9H-purine 

Relevant academic research and scientific papers

Synthesis of some substituted 6-phenyl purine analogues and their biological evaluation as cytotoxic agents

A series of 6-(4-substituted phenyl)-9-(tetrahydropyran-2-yl)purines 3–9, 6-(4-substituted phenyl)purines 10–16, 9-((4-substituted phenyl)sulfonyl)-6-(4-substituted phenyl)purines 17–32 were prepared and screened initially for their in vitro anticancer activity against selected human cancer cells (liver Huh7, colon HCT116, breast MCF7). 6-(4-Phenoxy-phenyl)purine analogues 9, 16, 30–32, had potent cytotoxic activities. The most active purine derivatives 5–9, 14, 16, 18, 28–32 were further screened for their cytotoxic activity in hepatocellular cancer cells. 6-(4-Phenoxyphenyl)-9-(tetrahydropyran-2-yl)-9H-purine (9) had better cytotoxic activity (IC50 5.4 μM) than the well-known nucleobase analogue 5-FU and known nucleoside drug fludarabine on Huh7 cells. The structure–activity relationship studies reported that the substitution at C-6 positions in purine nucleus with the 4-phenoxyphenyl group is responsible for the anti-cancer activity.

Aqueous-phase Suzuki-Miyaura cross-coupling reactions of free halopurine bases

The Suzuki-Miyaura reaction of 9-unsubstituted 2-, 6-, and 8-halopurine bases with diverse aryl- and alkenylboronic acids in water-acetonitrile mixtures under microwave irradiation was used for the single-step synthesis of arylpurines. In most cases the p

Cytostatic 6-arylpurine nucleosides II. Synthesis of sugar-modified derivatives: 9-(2-deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-deoxy-β-D-ribofuranosyl)- and 9-(2,3-dihydroxypropyl)-6-phenylpurines

9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-(4-substituted phenyl)purines, 9-(5-deoxy-β-D-ribofuranosyl)-6-(4-substituted phenyl)purines and 9-(2,3-dihydroxypropyl)-6-(4-substituted phenyl)purines were prepared by the Suzuki-Miyaura cross-coupling reactions of the corresponding protected 9-substituted 6-chloropurines with substituted phenylboronic acids followed by MeONa mediated deprotection. In contrast to the highly active 6-phenylpurine ribonucleosides, the title compounds did not show any considerable cytostatic activity.

Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: Application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids

The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6- chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a se

The Suzuki-Miyaura cross-coupling reactions of 6-halopurines with boronic acids leading to 6-aryl- and 6-alkenylpurines

The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine with boronic acids gave 6-alkylated purines in moderate to excellent yields. The best results with electron rich arylboronic acids were obtained in toluene in the presence of anhydrous

Synthesis and structure-activity relationships of 6-heterocyclic- substituted purines as inactivation modifiers of cardiac sodium channels

Purine-based analogs of SDZ 211-500 (5) were prepared and evaluated as inactivation modifiers of guinea pig or human cardiac sodium (Na) channels expressed in Xenopus oocytes. Substances which remove or slow the Na channel inactivation process in cardiac tissue are anticipated to prolong the effective refractory period and increase inotropy and thus have potential utility as antiarrhythmic agents. Heterocyclic substitution at the 6-position of the purine ring resulted in compounds with increased Na activity and potency, with 5-membered heterocycles being optimal. Only minor modifications to the benzhydrylpiperazine side chain were tolerated. Selected compounds which delayed the inactivation of Na channels were found to increase refractoriness and contractility in a rabbit Langendorff heart model, consistent with the cellular mechanism. Activity in both the oocyte and rabbit heart assays was specific to the S enantiomers. Preliminary in vivo activity has been demonstrated following intravenous infusion. The most promising compound on the basis of in vitro data is the formylpyrrole (S)74, which is 25-fold more potent than DPI 201-106 (1) in the human heart Na channel assay.

6-Chloropurines and organostannanes in palladium catalyzed cross coupling reactions

Carbon-carbon bond formation in the purine 6-position can easily be accomplished by palladium catalyzed cross coupling between 6-chloropurines and organostannanes without protection of the purine ring NH function. This technique provides a convenient route to cytokinines.

Synthesis of 6-Alkylpurine Derivatives by Nickel-comlex-catalyzed Coupling Reaction of 6-(Methylthio)purine Derivatives with Grignard Reagents

6-(Methylthio)purine reacted with RMgX (R=C6H5, CH3(CH2)nCH2 (n=2 to 6), C6H5CH2CH2, (CH3)2C=CHCH2CH2) in the presence of 5 molpercent in refluxing THF for 8h to afford 6-aryl or 6-alkylpurines in 62-74percent yields.By applying