109292-91-3

Basic information

• Product Name: N-cyclopentyl-9-methyl-9H-purin-6-amine
• Synonyms: 9H-purin-6-amine, N-cyclopentyl-9-methyl-; N-Cyclopentyl-9-methyl-9H-purin-6-amine
• CAS NO: 109292-91-3
• Molecular Formula: C₁₁H₁₅N₅
• Molecular Weight: 217.2703
• Mol File: 109292-91-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 426.9°C at 760 mmHg
• Flash Point: 212°C
• Density: 1.42g/cm³
• Vapor Pressure: 1.71E-07mmHg at 25°C
• Refractive Index: 1.738
• CAS DataBase Reference: N-cyclopentyl-9-methyl-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-cyclopentyl-9-methyl-9H-purin-6-amine(109292-91-3)
• EPA Substance Registry System: N-cyclopentyl-9-methyl-9H-purin-6-amine(109292-91-3)

Safety Data

• Hazardous Substances Data: 109292-91-3(Hazardous Substances Data)

Usage

General Description

N-cyclopentyl-9-methyl-9H-purin-6-amine is a chemical compound with a molecular formula of C11H16N4. It is a purine derivative and an aminopurine, which can be found in the class of adenosine receptor antagonists. N-cyclopentyl-9-methyl-9H-purin-6-amine is also known by the trade name Slikkagrel. It has been studied for its potential use in the treatment of cardiovascular diseases and other conditions, due to its ability to block adenosine receptors. Additionally, it has been investigated for its anti-inflammatory and antiplatelet effects, making it a potentially valuable compound for therapeutic use in various medical applications.

Upstream product

• 87-42-3 6-chloropurine 
• 2346-74-9 6-chloro-9-methyl-9H-purine 
• 1003-03-8 Cyclopentamine 

Relevant articles and documents

Synthesis and biological evaluation of disubstituted N6- cyclopentyladenine analogues: The search for a neutral antagonist with high affinity for the adenosine A1 receptor

Novel 3,8- and 8,9-disubstituted N6-cyclopentyladenine derivatives were synthesised in moderate overall yield from 6-chloropurine. The derivatives were made in an attempt to find a new neutral antagonist with high affinity for adenosine A1 receptors. N6-Cyclopentyl-9- methyladenine (N-0840) was used as a lead compound. Binding affinities of the new analogues were determined for human adenosine A1 and A 3 receptors. Their intrinsic activity was assessed in [ 35S]GTPγS binding experiments. Elongation of the 9-methyl of N-0840 to a 9-propyl substituent was very well tolerated. A 9-benzyl group, on the other hand, caused a decrease in adenosine A1 receptor affinity. Next, the 8-position was examined in detail, and affinity was increased with appropriate substitution. Most derivatives were A1-selective and 20 of the new compounds (6-9, 15-21, 23-26, 28, 31, 33, 35, and 36) had higher adenosine A1 receptor affinity than the reference substance, N-0840. Compound 31 (N6-cyclopentyl-8-(N-methylisopropylamino)-9- methyladenine, LUF 5608) had the highest adenosine A1 receptor affinity, 7.7 nM. In the [35S]GTPγS binding experiments, derivatives 5, 14, 22, 23, 25, 26, 33 and 34 did not significantly change basal [35S]GTPγS binding, thus behaving as neutral antagonists. Moreover, four of these compounds (23, 25, 26, and 33) displayed a 4- to 10-fold increased adenosine A1 receptor affinity (75-206 nM) compared to N-0840 (852 nM). In summary, we synthesised a range of N-0840 analogues with higher affinity for adenosine A1 receptors. In addition, four new derivatives, LUF 5666 (23), LUF 5668 (25), LUF 5669 (26) and LUF 5674 (33), behaved as neutral antagonists when tested in [ 35S]GTPγS binding studies. Thus, these compounds have improved characteristics as neutral adenosine A1 receptor antagonists.

N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor

N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors.The present study assessed the effect of N6 and N-9-substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide.The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > ethyl > methyl > 2-hydroxyethyl.The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor.An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold.The N6-cyclopentyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent.A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.