3444-09-5Relevant articles and documents
Synthesis of C-4′Truncated Phosphonated Carbocyclic 2′-Oxa-3′-azanucleosides as Antiviral Agents
Piperno, Anna,Giofre, Salvatore V.,Iannazzo, Daniela,Romeo, Roberto,Romeo, Giovanni,Chiacchio, Ugo,Rescifina, Antonio,Piotrowska, Dorota G.
, p. 2798 - 2805 (2010)
A new template of C-4′-truncated phosphonated nucleosides (TPCOANs) has been obtained in good yields according to two different routes which exploit the reactivity of a phosphonated nitrone. The one-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl nucleobases leads to the unnatural α-nucleosides as the main adducts. On the other hand, the target β-anomers have been obtained in high yield by a two-step procedure based on the 1,3-dipolar cycloaddition of a phosphonated nitrone with vinyl acetate followed by nucleosidation reaction. The reactivity of the phosphonated nitrone has been investigated trough quantum mechanical DFT calculations at the B3LYP/D95+(d,p) theory level. Preliminary biological assays show that β-anomers of TPCOANs are able to inhibit the reverse trancriptase of different retroviruses at concentrations in the nanomolar range, with a potency comparable with that of tenofovir.
Total synthesis of (+)-polyoxin J
Ghosh, Arun K.,Wang, Yong
, p. 2789 - 2795 (1999)
Stereoselective total synthesis of (+)-polyoxin J is described. The synthesis was achieved in a convergent manner by coupling protected thymine polyoxin C (19) and 5-O-carbamoyl polyoxamic acid 27 and subsequent removal of the protecting groups. The key steps of the synthesis of protected thymine polyoxin C involved the stereoselective electrophilic epoxidation of E-allyl alcohol 7 derived from isopropylidene D-ribose derivative 5, followed by regioselective epoxide opening of 8 and conversion of resulting azido diol 9 to protected thymine polyoxin C (19). Protected polyoxamic acid 27 was synthesized stereoselectively by utilizing Sharpless epoxidation of tartrate-derived allylic alcohol 20 followed by a regioselective epoxide ring opening with diisopropoxytitanium diazide.
Stereoselective nucleoside deuteration for NMR studies of DNA
Lukin, Mark,Santos, Carlos De Los
experimental part, p. 562 - 573 (2011/09/20)
A procedure has been elaborated for stereoselective deuterium substitution of one of the diastereotopic 5'-protons in 2'-deoxynucleotides. The synthetic scheme uses the reduction of the 5-oxosugar derivative with deuterated Alpine-Borane. The resulting de
Synthesis and antiviral activity of oxaselenolane nucleosides
Chu,Ma,Olgen,Pierra,Du,Gumina,Gullen,Cheng,Schinazi
, p. 3906 - 3912 (2007/10/03)
As dioxolane and oxathiolane nucleosides have exhibited promising antiviral and anticancer activities, it was of interest to synthesize isoelectronically substituted oxaselenolane nucleosides, in which the 3'-CH2 is replaced by a selenium atom. To study structure-activity relationships, various pyrimidine and purine oxaselenolane nucleosides were synthesized from the key intermediate, (±)-2-benzoyloxymethyl-1,2-oxaselenolane 5-acetate (6). Among the synthesized racemic nucleosides, cytosine and 5-fluorocytosine analogues exhibited potent anti-HIV and anti-HBV activities. It was of interest to obtain the enantiomerically pure isomers to determine if they have differential antiviral activities. However, due to the difficult and time-consuming nature of enantiomeric synthesis, a chiral HPLC separation was performed to obtain optical isomers from the corresponding racemic mixtures. Each pair of enantiomers of Se-ddC and Se-FddC was separated by an amylose chiral column using a mobile phase of 100% 2-propanol. The results indicate that most of the anti-HIV activity of both cytosine and fluorocytosine nucleosides resides with the (-)-isomers.
