715-91-3Relevant academic research and scientific papers
Synthetic strategies to 9-substituted 8-oxoadenines
Siah, Huey-San Melanie,Gundersen, Lise-Lotte
supporting information, p. 1469 - 1476 (2013/05/09)
Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction
Fletcher, Steven
experimental part, p. 2948 - 2950 (2010/06/21)
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.
Synthesis and antimicrobial evaluation of some new substituted purine derivatives
Tuncbilek, Meral,Ates-Alagoez, Zeynep,Altanlar, Nurten,Karayel, Arzu,Oezbey, Sueheyla
experimental part, p. 1693 - 1700 (2009/09/05)
A series of 8,9-disubstituted adenines (4, 5, 8), 6-substituted aminopurines (10-13) and 9-(p-fluorobenzyl/cyclopentyl)-6-substituted aminopurines (16, 17, 19-30) have been prepared and the antimicrobial activities of these compounds against Staphylococcu
8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
Lambertucci, Catia,Antonini, Ippolito,Buccioni, Michela,Dal Ben, Diego,Kachare, Dhuldeo D.,Volpini, Rosaria,Klotz, Karl-Norbert,Cristalli, Gloria
experimental part, p. 2812 - 2822 (2009/09/08)
Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio
An efficient Mitsunobu coupling to adenine-derived carbocyclic nucleosides
Yin, Xue-qiang,Li, Wei-kuan,Schneller, Stewart W.
, p. 9187 - 9189 (2007/10/03)
Adenine is a poor substrate for the Mitsunobu process to carbocyclic nucleosides. However, N-6 amino bis-Boc-protected adenine is reported herein to undergo an efficient coupling under these conditions as a result of its increased solubility and the reduc
N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor
Thompson, Robert D.,Secunda, Sherrie,Daly, John W.,Olsson, Ray A.
, p. 2877 - 2882 (2007/10/02)
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.
Purine Derivatives as Competitive Inhibitors of Human Erythrocyte Membrane Phosphatidylinositol 4-Kinase
Young, Rodney C.,Jones, Martin,Milliner, Kevin J.,Rana, Kishore K.,Ward, John G.
, p. 2073 - 2080 (2007/10/02)
The possibility of deriving a potent, cell-penetrating inhibitor of human erythrocyte PI 4-kinase, competitive with respect to ATP, has been investigated in a series of purine derivatives and analogues.The purine nucleus is not essential for binding to th
