88492-34-6Relevant articles and documents
Synthesis and cytotoxic activity of novel acyclic nucleoside analogues with functionality in click chemistry
G?adysz, Micha?,Ruszkowski, Piotr,Milecki, Jan
, p. 53 - 66 (2018/02/14)
We describe synthesis of novel acyclic nucleoside analogues which are building blocks for CuAAC reaction and their activity against two types of human cancer cell lines (HeLa, KB). Three of chosen compounds show promising cytotoxic activity. Synthesis pathway starting from simple and easily accessible substrates employing DMT or TBDPS protective groups is described. Adenosine and thymidine analogues containing alkyne moiety and adenosine analogue containing azido group were synthesized. The obtained units showed ability of forming triazole motif under the CuAAC reaction conditions.
SYNTHESIS OF 3-AMINO- AND 3-AZIDOANALOGS OF 9-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)ADENINE (HPMPA)
Holy, Antonin
, p. 446 - 454 (2007/10/02)
1-Azidopropane-2,3-diol (IIb) reacts with p-toluenesulfonyl chloride to give the tosyl derivative IIIa which, on acid catalyzed condensation with 2,3-dihydropyran, afforded 1-azido-2-(tetrahydropyran-2-yloxy)-3-(p-toluenesulfonyloxy)propane (IIIb).Treatment of adenine sodium salt with IIIb resulted in the intermediate IV which was transformed by acid hydrolysis to 9-(RS)-(3-azido-2-hydroxypropyl)adenine (V).Catalytic hydrogenation of V led to 9-(RS)-(3-amino-2-hydroxypropyl)adenine (VI). 9-(RS)-(3-Azido-2-hydroxypropyl)-N(6)-benzoyladenine (VII) was obtained from V bychlorotrimethylsilane/benzoyl chloride treatment.Reaction of the compound VII with dimethyl p-toluenesulfonyloxymethanephosphonate (VIII) in the presence of excess sodium hydride, followed by alkaline hydrolysis, afforded methyl 9-(3-azido-2-phosphonylmethoxypropyl)adenine (IXa) which was transformed to the parent acid IXb by bromotrimethylsilane treatment.Hydrogenolysis of IXb yielded 9-(RS)-(3-amino-2-phosphonylmethoxypropyl)-adenine (X).
