41552-82-3

Basic information

• Product Name: N6-CYCLOPENTYLADENOSINE
• Synonyms: N6-CYCLOPENTYLADENOSINE;N-CYCLOPENTYLADENOSINE;N(sup 6)-cyclopentyladenosine;Adenosine, N-cyclopentyl-;N6-Cyclopentyladenosine,CPA;(2R,3R,4S,5R)-2-(6-(CyclopentylaMino)-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;N6-Cyclopentyladenosine
• CAS NO: 41552-82-3
• Molecular Formula: C₁₅H₂₁N₅O₄
• Molecular Weight: 335.36
• Product Categories: Adenosine receptor
• Mol File: 41552-82-3.mol

Chemical Properties

• Boiling Point: 673.4 °C at 760 mmHg
• Flash Point: 361.1 °C
• Appearance: white to off-white/
• Density: 1.78 g/cm³
• Vapor Pressure: 4.71E-19mmHg at 25°C
• Refractive Index: 1.816
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble1.7mg/mL
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: N6-CYCLOPENTYLADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N6-CYCLOPENTYLADENOSINE(41552-82-3)
• EPA Substance Registry System: N6-CYCLOPENTYLADENOSINE(41552-82-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 41552-82-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
N6-Cyclopentyladenosine is used as a selective agonist for studying the effects on adenosine receptors, particularly A1, A2A, and A3 receptors. Its application in this field aids in understanding the role of these receptors in various physiological processes and potential therapeutic interventions.
Used in Organophosphate Toxicity Research:
N6-Cyclopentyladenosine is used as a therapeutic agent for studying its efficacy against organophosphate toxicity. This application helps in exploring potential treatments for poisoning caused by organophosphate compounds.
Used in Smooth Muscle Cell Research:
N6-Cyclopentyladenosine is used as a research tool to study its effects on cavernosal smooth muscle cells from lean and db/db (obesity and type II diabetes caused by a leptin receptor mutation) mice. This application contributes to the understanding of the compound's impact on smooth muscle cell function in the context of obesity and type II diabetes.

Biological Activity

Potent and selective adenosine A 1 receptor agonist (K i values are 2.3, 790 and 43 nM for human A 1 , A 2A and A 3 receptors respectively; EC 50 = 18600 nM for hA 2B ). Centrally active following systemic administration in vivo .

Biochem/physiol Actions

N6-Cyclopentyladenosine (CPA) is an adenosine derivative and a potent A1 adenosine receptor agonist. It acts as an anticonvulsant and might exhibit protective actions against aminophylline (AMPH)-induced seizures.

InChI:InChI=1/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 1003-03-8 Cyclopentamine 
• 64344-19-0 N⁶-chloro-adenosine 
• 1229622-80-3 C₄₂H₄₇N₅O₆ 
• 14426-53-0 6-Iodo-purine riboside 
• 58-61-7 adenosine 
• 3056-18-6 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 
• 37739-05-2 2-chloro-N⁶-cyclopentyladenosine 

Downstream Products

• 581106-44-7 Cyclopentyl-{9-[(3aR,4R,6S,6aS)-6-(2-fluoro-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-amine 
• 871108-05-3 ((2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate 
• 151563-25-6 Carbonic acid benzyl ester (3aR,4R,6R,6aR)-6-(6-cyclopentylamino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 199587-01-4 5'-tosyl-2',3'-di-O-benzoyl-N⁶-cyclopentyladenosine 
• 199587-00-3 2',3'-di-O-benzoyl-N⁶-cyclopentyladenosine 
• 197796-86-4 (2R,3R,4R,5S)-4-Azido-2-(6-cyclopentylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol 
• 365533-71-7 3,4,5-trimethoxy-benzoic acid 6-(6-cyclopentylamino-purin-9-yl)-2-ethoxy-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 

Relevant articles and documents

First no-carrier-added radioselenation of an adenosine-A1 receptor ligand

The precursor synthesis and the no-carrier-added (n.c.a.) radiosynthesis of the adenosine-A1 receptor ligand 5′-(methyl[ 75Se]seleno)-N6-cyclopentyladenosine ([75Se]1) are described in this report. A method was developed starting from elemental n.c.a. selenium-75, followed by a three-step polymer-supported radioselenation and deprotection which gave the radioligand with a radiochemical yield of 30%, a radiochemical purity of > 99% and a specific radioactivity of > 300 GBq/mmol (8 Ci/mmol). Preparation time was 40 min. The nonradioactive compound 5′-(methylseleno)-N6-cyclopentyladenosine (1) was pharmacologically evaluated in vitro and showed high affinity and selectivity for the adenosine-A1 receptor. These preliminary results suggest that this compound could be a useful radioligand for the noninvasive imaging of the brain adenosine-A1 receptors using positron emission tomography (PET) when labelled with the positron emitter selenium-73 (half-life: 7.1 h). Copyright

Synthesis and ability of new ligands for G protein-coupled receptors 17 (GPR17)

Background: GPR17 is believed to be a novel target for the development of new therapeutic approaches to human stroke and multiple sclerosis. Hence, the selection of GPR17 ligands may be a potent way to reduce the progression of ischemic damage. Material/Methods: New potential ligands for GPR17, mono-, di-, and triphosphate adenosine nucleotides substituted at N6-position with a methyl and a cyclopentyl group were synthesized. The ability of new ligands to bind GPR17 was evaluated using frontal affinity chromatography-mass spectrometry (FAC-MS) method. Cangrelor, MRS2179, and uridine diphosphate were selected as the reference compounds. Results: The new triphosphate derivatives 9 and 10 were considered as the new GPR17 ligands. The compound 10 was eluted with breakthrough time (bt) between cangrelor and MRS 2179 (compound 10, bt=12.25; cangrelor, bt=24.55, and MRS 2179, bt=7.10), while the breakthrough volume of compound 9 was similar to that of MRS 2179 (compound 9, bt=7.53 and MRS 2179, bt=7.10). Conclusions: N6-cyclopentyATP 10 is medium-high affinity ligand of GPR17, while the corresponding N6-methyl derivative 9 is a medium affinity ligand similar to MRS 2179. Hence, the new N6-cyclopentylATP 10 might be a good candidate for the pharmacological characterization of GPR17.

METHODS OF PREVENTING, REDUCING OR TREATING MACULAR DEGENERATION

The present invention is directed to selective adenosine A1 agonist compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, reduce or prevent age-related macular degeneration.

METHOD OF PROVIDING OCULAR NEUROPROTECTION

Provided herein are compounds of Formula I, compositions comprising an effective amount of a compound of Formula I, and methods for preventing, reducing or treating retinal ganglion cell damage comprising administering an effective amount of a purine deri

OPHTHALMIC FORMULATIONS

The present invention relates to an ophthalmic formulation which comprises a fine particle of Compound A in an aqueous suspension and a manufacturing process thereof. More specifically, the present invention relates to a topically applied ophthalmic aqueous suspension which is obtainable by suspending fine particles of Compound A in an aqueous vehicle containing a surfactant and boric acid. The invention also provides processes for making the ophthalmic formulations and to methods of use thereof.

ANHYDROUS POLYMORPHS OF [(2R,3S,4R,5R)-5-(6-(CYCLOPENTYLAMINO)-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YL)} METHYL NITRATE AND PROCESSES OF PREPARATION THEREOF

The present invention provides novel anhydrous polymorph forms of 2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate (Compound A). The present invention also provides processes for preparation of the anhydrous polymorphic forms of compound A.

COMBINATION, KIT AND METHOD OF REDUCING INTRAOCULAR PRESSURE

The present invention is directed to a combination or a kit comprising a prostaglandin analog and an adenosine receptor A1 agonist and to a method of reducing intraocular pressure (IOP) in a subject using such combination or kit. The invention is particularly directed to a combination of latanoprost marketed under the brand Xalatan? and Compound A.

Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction

A novel synthetic route to N6-substitution of adenine is presented, employing the Mitsunobu reaction as the key step. A range of primary and secondary alcohols all coupled in very good to excellent yields within 30 min at 45 °C, offering a milder alternative to the traditional nucleophilic aromatic substitution of 6-chloropurine. The utility of this protocol is further demonstrated by its application to the syntheses of N6,N9-di-substituted adenines, including the potent and selective A1 adenosine receptor agonist N6-cyclopentyladenosine.

N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity

A series of adenosine analogues differently substituted in N 6-position were synthesized to continue our studies on the relationships between structure and biological activity of iPA. The structures of the compounds were confirmed by standard studies of 1H NMR, MS and elemental analysis. These molecules were then evaluated for their anti-proliferative activity on bladder cancer cells. We found that some of these compounds possess anti-proliferative activity but have no effect on cell invasion and metalloprotease activity.

METHOD OF REDUCING INTRAOCULAR PRESSURE IN HUMANS

Provided herein are compounds of Formula I, compositions comprising an effective amount of a compound of Formula I, and methods for reducing intraocular pressure comprising administering an effective amount of compounds of Formula I to a subject in need t