103626-36-4

Basic information

• Product Name: 9H-Purin-6-amine, N-cyclopentyl-
• Synonyms: 9H-Purin-6-amine, N-cyclopentyl-
• CAS NO: 103626-36-4
• Molecular Formula: C₁₀H₁₃N₅
• Molecular Weight: 0
• Mol File: 103626-36-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9H-Purin-6-amine, N-cyclopentyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Purin-6-amine, N-cyclopentyl-(103626-36-4)
• EPA Substance Registry System: 9H-Purin-6-amine, N-cyclopentyl-(103626-36-4)

Safety Data

• Hazardous Substances Data: 103626-36-4(Hazardous Substances Data)

Upstream product

• 87-42-3 6-chloropurine 
• 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.

Synthesis of 4-hydroxy-3-[(E)-2-(6-substituted-9H-purin-9-yl)vinyl] coumarins as lipoxygenase inhibitors

The synthesis of 4-hydroxy-3-[(E)-2-(6-substituted-9H-purin-9-yl)vinyl] coumarins has been achieved from the reactions of 4-hydroxycoumarin with 2-(6-substituted-9H-purin-9-yl)acetaldehydes in DMF under heating. The new compounds showed significant lipoxy

Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)

The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

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.

Inhibitors of MAPK/Erk Kinase

The present invention relates to compounds useful as inhibitors of MEK kinase and methods for the treatment or prevention of cellular proliferative disease states, such as conditions related to the hyperactivity of MEK, as well as diseases modulated by the MEK cascade.