54262-83-8Relevant academic research and scientific papers
Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
Qin, Tao,Li, Jian-Ping,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming
supporting information, p. 15512 - 15523 (2019/01/04)
An efficient method to construct chiral acyclic nucleosides via Sharpless asymmetric dihydroxylation of N-allylpyrimidines or N-alkenylpurines is reported. A range of chiral acyclic nucleosides with two adjacent hydroxyl groups present on the side chains could be produced in good yields (up to 97% yield) and excellent enantioselectivities (90-99% ee). The synthetic utility of the reaction was demonstrated by the catalytic asymmetric synthesis of (S)-Cidofovir and (R)-Buciclovir.
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.
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
Enantiomeric radiochemical synthesis of R and S (1-(6-amino-9H-purin-9-yl)- 3-fluoropropan-2-yloxy)methylphosphonic acid (FPMPA)
Kiesewetter, Dale O.,Knudson, Kathleen,Collins, Matt,Srinivasula, Sharat,Lim, Esther,Di Mascio, Michele
, p. 187 - 194 (2008/09/19)
Therapy for human immunodeficiency virus (HIV)-infected patients requires chronic multidrug administration. The eventual failure of therapy in some patients has brought into question the tissue concentration of the drugs. With an appropriately radiolabele
The nucleoside transport proteins, NupC and NupG, from Escherichia coli: Specific structural motifs necessary for the binding of ligands
Patching, Simon G.,Baldwin, Stephen A.,Baldwin, Alexander D.,Young, James D.,Gallagher, Maurice P.,Henderson, Peter J. F.,Herbert, Richard B.
, p. 462 - 470 (2007/10/03)
A series of 46 natural nucleosides and analogues (mainly adenosine-based) were tested as inhibitors of [U-14C]uridine uptake by the concentrative, H+-linked nucleoside transport proteins NupC and NupG from Escherichia coli. The two evolutionarily unrelated transporters showed similar but distinct patterns of inhibition, revealing differing selectivities for the different nucleosides and their analogues. Binding of nucleosides to NupG required the presence of hydroxyl groups at each of the C-3′ and C-5′ positions of ribose, while binding to NupC required only the C-3′ hydroxyl substituent. The greater importance of the ribose moiety for binding to NupG is consistent with the evolutionary relationship between this protein and the oligosaccharide: H+ symporter (OHS) subfamily of the major facilitator superfamily (MFS) of transporters. For both proteins the natural α-configuration at C-3′ and the natural β-configuration at C-1′ was mandatory for ligand binding. N-7 in the imidazole ring of adenosine and the amino group at C-6 were found not to be important for binding and both transporters showed flexibility for substitution at C-6/N6; one or both of N-l and N-3 were important for adenosine analogue binding to NupC but significantly less so for binding to NupG. From the different effects of 8-bromoadenosine on the two transporters it appears that adenosine selectively binds to NupC in an anti- rather than a syn-conformation, whereas NupG is less prescriptive. The pattern of inhibition of NupC by differing nucleoside analogues confirmed the functional relationship of the bacterial transporter to members of the human concentrative nucleoside transporter (CNT) family and reaffirmed the use of the bacterial protein as an experimental model for these physiologically and clinically important mammalian proteins. The specificity data for NupG have been used to develop a homology model of the protein's binding site, based on the X-ray crystallographic structure of the disaccharide transporter LacY from E. coli. We have also developed an efficient general protocol for the synthesis of adenosine and three of its analogues, which is illustrated by the synthesis of [1′-13C]adenosine.
A new approach to the synthesis of optically active alkylated adenine derivatives
Zakirova,Shipitsyn,Belanov,Jasko
, p. 3357 - 3360 (2007/10/03)
A new synthesis of chiral acyclic nucleoside and nucleotide analogues starting from D(-)- or L(+)-riboses was proposed. Antiviral properties of the synthesized compounds towards the pox virus family were evaluated.
Synthesis of propane-2,3-diol combinatorial monomers
Acevedo, Oscar L.,Andrews, Robert S.
, p. 3931 - 3934 (2007/10/03)
Base catalyzed reaction of heterocyclic bases with R-(+)-glycidol gives heteroaryl-propane-2,3-diols which are functionalized to the 3-O-dimethoxytrityl-2-O-phosphoramidites. A dimethoxytrityl-glycidol is reacted with alkyl or aryl Grignard reagents and then phosphitylated to yield 1-O-dimethoxytrityl-2-phosphoramidites. These compounds can be used for combinatorial oligomer synthesis.
Dioxolane nucleosides and their phosphonate derivatives: synthesis and hydrolytic stability
Efimtseva, Ekaterina V.,Mikhailov, Sergey N.,Mashkov, Sergey,Hankamaeki, Teemu,Oivanen, Mikko,Loennberg, Harri
, p. 1409 - 1416 (2007/10/02)
Several new nucleoside (12-15) and nucleoside phosphonate (27-30) analogues derived from (+/-)-cis- and -trans-2-hydroxymethyl-4-methyl-1,3-dioxolane have been prepared and their configurations assigned by 1H NMR spectroscopy.First-order rate constants fo
Reaction of 8-Substituted Adenines with Glycidol
Ratsino, E. V.,Radchenko, S. I.
, p. 273 - 275 (2007/10/03)
The regioselectivity of isomer formation in the reaction of 8-substituted adenines with glycidol depends on steric factors of substituents.The compounds prepared were tested for immunostimulating activity.
