85110-23-2

Basic information

• Product Name: 1H-Purine, 6-(phenylethynyl)-
• Synonyms: 6-phenylethynylpurine
• CAS NO: 85110-23-2
• Molecular Formula: C13H8N4
• Molecular Weight: 220.233
• Mol File: 85110-23-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Purine, 6-(phenylethynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Purine, 6-(phenylethynyl)-(85110-23-2)
• EPA Substance Registry System: 1H-Purine, 6-(phenylethynyl)-(85110-23-2)

Safety Data

• Hazardous Substances Data: 85110-23-2(Hazardous Substances Data)

Usage

Classification

Purine class of organic compounds.

Derivative

A derivative of purine with a phenylethynyl substituent at the 6-position.

Structure

Heterocyclic aromatic organic compound.

Distribution

Widely distributed in nature.

Biological significance

Important functions in the biochemistry of living organisms.

Pharmacological properties

Potential pharmacological properties, particularly in the context of neurological and psychiatric disorders.

Receptor interaction

Potent and selective antagonist of A1 adenosine receptors.

Implications

A1 adenosine receptors are implicated in the regulation of neurotransmitter release and neuromodulation.

Therapeutic applications

Potential treatment of conditions such as anxiety, depression, and neurodegenerative diseases.

Upstream product

• 2545-26-8 6-iodopurine 
• 536-74-3 phenylacetylene 
• 71819-06-2 6-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 451455-08-6 6-phenylethynyl-9-(tetrahydro-pyran-2-yl)-9H-purine 
• 87-42-3 6-chloropurine 

Downstream Products

• 1027239-86-6 9-Oxiranylmethyl-6-phenylethynyl-9H-purine 
• 91077-87-1 (Z)-6-(2-bromo-2-phenylethenyl)purine 
• 91077-86-0 (Z)-6-(2-chloro-2-phenylethenyl)purine 
• 54108-66-6 6-(2-phenethyl)purine 

Relevant articles and documents

Suzuki-miyaura and sonogashira coupling of 6-chloropurines and-nucleosides in water

A general protocol is reported for the efficient Suzuki-Miyaura and the copper-free Sonogashira coupling of unprotected 6-chloropurines and unprotected β-D-ribofuranosyl-6-chloropurine in water or in water/n-butanol utilizing Na2PdCI4/sub

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.