55559-72-3Relevant 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.
A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives: Formal synthesis of naturally occurring norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine
Saha,Chakraborty,Roy
, p. 837 - 846 (2014/07/07)
A concise and simple synthesis of 1-hydroxy-phenethylamine derivatives has been achieved following classical organic transformations using commercially available chiral pools. The said derivatives were explored for the synthesis of naturally occurring bio-active small molecules. Formal synthesis of norephedrine, virolin and 3-hydroxy-2-phosphonylmethoxypropyl adenine has been demonstrated.
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
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.
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.
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
SYNTHESES OF ENANTIOMERIC N-(3-HYDROXY-2-PHOSPHONOMETHOXYPROPYL)DERIVATIVES OF PURINE AND PYRIMIDINE BASES
Holy, Antonin
, p. 649 - 674 (2007/10/02)
Methods of preparation of N-(3-hydroxy-2-phosphonomethoxypropyl) (HPMP) derivatives of (2S)- and (2R)-configuration compounds I and XXVII, respectively are described.The general method starts from the corresponding N-(2,3-dihydroxypropyl) derivatives which were converted either into the (R)-enantiomers XIII by reaction of the base with (R)-glycidol butyrate (XII) in the presence of cesium carbonate and subsequent methanolysis, or into the (S)-enantiomers XI by alkylation of the base with (R)-2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane (V) in the presence of the same reagent.The amino groups on the heterocyclic base in compounds XI and XIII were benzoylated by silylation followed by reaction with benzoyl chloride and the obtained N-benzoates XV and XVII on reaction with trityl chloride afforded the corresponding 3'-O-trityl derivatives XVI and XVIII.These compounds were condensed with bis(2-propyl)-p-toluenesulfonyloxymethanephosphonate (XXIII) in dimethylformamide in the presence of sodium hydride to give the fully protected diesters XXIV and XXVIII.These compounds could be selectively acid-hydrolyzed to remove the trityl group only under formation of compounds XXXV, or methanolyzed and then acid-hydrolyzed to remove the trityl and N-benzoyl groups and lead to compounds XXVI and XXX, or treated with bromotrimethylsilane to remove the trityl and 2-propyl group to give phosphonates of the type XXVI.All the three types of compounds were then converted into free phosphonates of the (S)-series (I) and (R)-series (XXVII).Derivatives of cytosine (Ia, XXVIIa), adenine (Ib, XXVIIb), 2,6-diaminopurine (Ic, XXVIIc) and guanine (Id, XXVIId) were prepared.Condensation of the partially blocked adenine derivative XXXV with the tosyl derivative XXIII and subsequent deprotection afforded 9-(S)-(2,3-diphosphonomethoxypropyl)adenine (XLIII).Reaction of the same compound XXXV or its (R)-enantiomer XXXVIII with diethyl chlorophosphonate, followed by deblocking, afforded 3'-O-phosphoryl derivatives (S)-HPMPA (XXXVII) and (R)-HPMPA (XL).
EASY ALKYLATION OF PURINE BASES BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT SOLVENT. STRUCTURAL ANALYSIS BY 2D HETERONUCLEAR 1H 13C CORRELATED NMR SPECTROSCOPY
Platzer, Nicole,Galons, Herve,Bensaid, Younes,Miocque, Marcel,Bram, Georges
, p. 2101 - 2108 (2007/10/02)
Solid-liquid PTC without added organic solvent promotes alkylation of purine derivatives leading in particular to an efficient synthesis of the antiviral DHPA.The location of the substituent on the ring was determined by analysis of coupling interactions
