23589-16-4Relevant articles and documents
A highly facile and efficient one-step synthesis of N6-adenosine and N6-2′-deoxyadenosine derivatives
Wan, Zhao-Kui,Binnun, Eva,Wilson, Douglas P.,Lee, Jinbo
, p. 5877 - 5880 (2005)
(Chemical Equation Presented) A highly facile and efficient one-step synthesis of N6-adenosine and N6-2′-deoxyadenosine derivatives has been developed. Treatment of inosine or 2′-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6- adenosine and N6-2′-deoxyadenosine derivatives in good to excellent yields. Carcinogenic polyaromatic hydrocarbon (PAH) N 6-2′-deoxyadenosine adduct 10 and a rare DNA constituent 11 were thus synthesized directly from 2′-deoxyinosine both in 98% yield.
Modification of the length and structure of the linker of N6-benzyladenosine modulates its selective antiviral activity against enterovirus 71
Drenichev, Mikhail S.,Oslovsky, Vladimir E.,Sun, Liang,Tijsma, Aloys,Kurochkin, Nikolay N.,Tararov, Vitali I.,Chizhov, Alexander O.,Neyts, Johan,Pannecouque, Christophe,Leyssen, Pieter,Mikhailov, Sergey N.
, p. 84 - 94 (2016/02/18)
Very recently, we demonstrated that N6-isopentenyladenosine, a cytokinin nucleoside, exerts a potent and selective antiviral effect on the replication of human enterovirus 71. The present study is devoted to the structure optimization of another natural compound: N6-benzyladenosine. We mainly focused on the exploration of the size and nature of the linker between the adenine and the phenyl ring, as well as on the necessity of the D-ribose residue. More than 30 analogues of N6-benzyladenosine were prepared and their antiviral properties were evaluated. Two main methodologies were used for preparation: N6-acetyl-2′,3′,5′-tri-O-acetyladenosine can be regioselectively alkylated either by alkyl halides under base promoted conditions or by alcohols in Mitsunobu reactions. After deacylation with 4 M PrNH2 in MeOH at room temperature for one day, the desired products were obtained in overall high yields. Analysis of the structure-activity relationship clearly shows that the optimal size of the linker is limited to 2 or 3 atoms (compounds 4-7). 2′-Deoxyadenosine derivatives did not elicit any inhibitory or cytotoxic effect, while 5′-deoxynucleosides still induced some cell protective antiviral activity. Based on these observations, it can be hypothesized that there may be another mechanism that is at the base of the antiviral activity of these compounds against enterovirus 71 besides a possible 5′-triphosphorylation followed by a putative inhibitory effect on RNA synthesis.
Site-selective direct arylation of unprotected adenine nucleosides mediated by palladium and copper: insights into the reaction mechanism
Storr, Thomas E.,Firth, Andrew G.,Wilson, Karen,Darley, Kate,Baumann, Christoph G.,Fairlamb, Ian J.S.
, p. 6125 - 6137 (2008/09/21)
Reaction conditions facilitating the site-selective direct aryl functionalisation at the C-8 position of adenine nucleosides have been identified. Many different aromatic components may be effectively cross-coupled to provide a diverse array of arylated adenine nucleoside products without the need for ribose or adenine protecting groups. The optimal palladium catalyst loading lies between 0.5 and 5 mol %. Addition of excess mercury to the reaction had a negligible affect on catalysis, suggesting the involvement of a homogeneous catalytic species. A study by transmission electron microscopy (TEM) shows that metal containing nanoparticles, ca. 3 nm with good uniformity, are formed during the latter stages of the reaction. Stabilised PVP palladium colloids (PVP=N-polyvinylpyrrolidone) are catalytically active in the direct arylation process, releasing homogenous palladium into solution. The effect of various substituted 2-pyridine ligand additives has been investigated. A mechanism for the site-selective arylation of adenosine is proposed.
