20125-39-7Relevant articles and documents
A molecular target for suppression of the evolution of antibiotic resistance: Inhibition of the Escherichia coli RecA protein by N 6-(1-naphthyl)-ADP
Lee, Andrew M.,Ross, Christian T.,Zeng, Bu-Bing,Singleton, Scott F.
, p. 5408 - 5411 (2005)
We report that N6-(1-naphthyl)-ADP (1) inhibits the Escherichia coli RecA protein in vitro. A novel rapid screen identified 1 as a potent inhibitor of RecA nucleoprotein filament formation, and further characterization established 1 as an ATP-competitive inhibitor of RecA-catalyzed ATP hydrolysis. 1 and other inhibitors of RecA activities represent a new approach for understanding the molecular targets and pathways involved in the evolution of antibiotic resistance in bacteria.
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.
N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity
Ottria, Roberta,Casati, Silvana,Baldoli, Erika,Maier, Jeanette A.M.,Ciuffreda, Pierangela
experimental part, p. 8396 - 8402 (2011/02/22)
A series of adenosine analogues differently substituted in N 6-position were synthesized to continue our studies on the relationships between structure and biological activity of iPA. The structures of the compounds were confirmed by standard studies of 1H NMR, MS and elemental analysis. These molecules were then evaluated for their anti-proliferative activity on bladder cancer cells. We found that some of these compounds possess anti-proliferative activity but have no effect on cell invasion and metalloprotease activity.