26524-60-7Relevant articles and documents
Synthesis and cytotoxic activity of novel 5-substituted-1-(β-L- arabinofuranosyl) pyrimidine nucleosides
Sendula, Robert,Orban, Erika,Hudecz, Ferenc,Sagi, Gyula,Jablonkai, Istvan
experimental part, p. 482 - 500 (2012/07/28)
A series of new 5-halogeno-1-(β-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)- ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 μM concentrations. Copyright Taylor and Francis Group, LLC.
Synthesis of 1-β-L-arabinofuranosylcytosine (β-L-Ara-C) and 2'-deoxy- 2'-methylene-β-L-cytidine (β-L-DMDC) as potential antineoplastic agents
Lin,Luo,Liu
, p. 1861 - 1870 (2007/10/02)
1-β-L-Arabinofuranosylcytosine (β-L-Ara-C, 7) and 2'-deoxy-2'-methylene- β-L-cytidine (β-L-DMDC, 14) have been synthesized via a multi-step synthesis from L-arabinose. These compounds were tested in vitro against L1210, P388, Sarcoma 180, and CEM cells, and found not to be active at a concentration up to 100 μM. β-L-Ara-C and β-L-DMDC were also tested against HSV-1 and HSV-2 and yielded ID50 values of >100 μM.
CONFORMATIONAL PARAMETERS OF THE CARBOHYDRATE MOIETIES OF α-ARABINONUCLEOSIDES
Ekiel, Irena,Darzynkiewicz, Edward,Shugar, David
, p. 21 - 36 (2007/10/02)
The conformations of the sugar moieties of a number of α-D- and -L-arabinofuranosyl nucleosides in solution have been investigated, largely with the aid of a statistical procedure developed for this purpose.The overall results demonstrated the existence, for a broad range of analogs, of a two-state, conformational equilibrium, NS (or 2E3E).As between different analogs, there is a large variation in the relative populations of these two states that is related to the nature of the aglycon, the type of protecting groups on the sugar hydroxyl groups, and, to a much smaller extent, the solvent system.There is a striking correlation between the conformation of the sugar and the orientation of the exocyclic, hydroxymethyl group.Both for purine and pyrimidine nucleosides, a preponderance of the gauche-gauche rotamer of the exocyclic group is associated with the type-N state of the furanose ring, whereas, with the type-S state, the gauche-gauche rotamer population is virtually nonexistent.A comparison with X-ray diffraction data for 9-α-D-arabinofuranosyladenine demonstrated that, as for other classes of nucleosides, the solid-state conformation corresponds to one of the states participating in the equilibrium in solution.
