56046-34-5Relevant academic research and scientific papers
NMR and X-ray structural studies on 3-benzyl-8-bromoadenine
Siah, Huey-San Melanie,Goerbitz, Carl Henrik,Gundersen, Lise-Lotte
, p. 1375 - 1378 (2011)
8-Bromoadenine was benzylated in the presence of base to give a mixture of two regioisomers. One was easily recognized as 9-benzyl-8-bromoadenine, but the other structure could not be determined with absolute certainty by NMR. Therefore, X-ray crystallogr
Synthetic strategies to 9-substituted 8-oxoadenines
Siah, Huey-San Melanie,Gundersen, Lise-Lotte
, 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.
NOVEL ANTIBACTERIAL COMPOUNDS
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Page/Page column 19, (2012/07/14)
The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1. The compounds are useful in the prevention and/or treatment of bacterial infections.
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
Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family
Borrmann, Thomas,Abdelrahman, Aliaa,Volpini, Rosaria,Lambertucci, Catia,Alksnis, Edgars,Gorzalka, Simone,Knospe, Melanie,Schiedel, Anke C.,Cristalli, Gloria,Müller, Christa E.
scheme or table, p. 5974 - 5989 (2010/03/24)
Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.
DIKETO ACIDS WITH NUCLEOBASE SCAFFOLDS: ANTI-HIV REPLICATION INHIBITORS TARGETED AT HIV INTEGRASE IN COMBINATION THERAPY
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, (2008/06/13)
A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HFV and in the treatmen
Diketo acids with nucleobase scaffolds: anti-HIV replication inhibitors targeted at HIV integrase
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Page/Page column 24, (2008/06/13)
A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HIV and in the treatmen
Diketo acids on nucleobase scaffolds as inhibitors of Flaviviridae
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Page/Page column 25, (2010/11/24)
A new class of diketo acids constructed on nucleobase scaffolds, designed as inhibitors of HCV replication through inhibition of HCV NS5B RNA polymerase, is described. These compounds are useful in the prevention or treatment of infection by HCV and in th
PHOSPHODIESTERASE INHIBITORS
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Page/Page column 33, (2008/06/13)
The present invention relates to purine derivatives, which can be used as selective phosphodiesterase (PDE) type IV inhibitors. Compounds disclosed herein can be useful in the treatment of asthma, arthritis, bronchitis, chronic obstructive pulmonary disease (COPD), psoriasis, allergic rhinitis, shock, atopic dermatitis, Crohn's disease, adult respiratory distress syndrome (ARDS), eosinophilic granuloma, allergic conjunctivitis, osteoarthritis, ulcerative colitis and other inflammatory diseases especially in humans. Also provided are processes for the preparation of disclosed compounds, pharmaceutical composition containing the disclosed compounds and their use as selective phosphodiesterase (PDE) type IV inhibitors.
The Suzuki-Miyaura cross-coupling reactions of 2-, 6- or 8-halopurines with boronic acids leading to 2-, 6- or 8-aryl- and -alkenylpurine derivatives
Havelkova,Dvorak,Hocek
, p. 1704 - 1710 (2007/10/03)
The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine, 9- or 3-benzyl-8-bromoadenine and 2,6-dihalopurines with boronic acids gave the corresponding 6-, 8- or 2-aryl- or -alkenylpurines in good yields. Anhydrous conditions in toluene were
