Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

• Lucie Brulikova and
• Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

• by fluorine have been investigated as potent anticancer agents since the 1960s. Nevertheless, many such modified compounds were also synthesized in order to investigate their antiviral activity. As a consequence of interest in biologically active fluoro derivatives, Bergstrom and co-workers carried

• activity and especially their antiviral activity. In 1989 Kumar and co-workers reported, amongst other things, two 5-(1-methoxy-2-haloethyl)-2'-deoxyuridines 12 and 13 (Scheme 3) [9]. Their synthesis was based on the addition of HOX (X = Br, Cl) to the vinyl moiety of 5-vinyl-2'-deoxyuridine (9). The

• CH3OX (X = Cl, Br or I) to the vinyl moiety of (E)-5-(2-halovinyl)-2'-deoxyuridine. Rai and co-workers developed an efficient synthesis of 5-[1-(2-halo(or nitro)ethoxy)-2-iodoethyl]-2'-deoxyuridines 50–54 (Scheme 8) and evaluated their antiviral activity [16]. For this purpose, 5-vinyl-2'-deoxyuridine

Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide

• Nikola Cindro,
• Margareta Horvat,
• Kata Mlinarić-Majerski,
• Axel G. Griesbeck and
• Nikola Basarić

Beilstein J. Org. Chem. 2011, 7, 270–277, doi:10.3762/bjoc.7.36

• activity [53][54][55]. Thus, photoproducts derived from 5 may also exhibit antiviral activity, although that is yet to be substantiated. Results and Discussion The synthesis of homoadamantylphthalimide 5 started from homoadamantanone 3 which is easily prepared by the ring enlargement of adamantanone with

• ring closure to azetidinols and ring enlargement to azepinediones. High selectivity and high isolable yield of 6 in the photoreaction of 5 makes this photoinduced C–H activation useful in the synthesis of very complex derivatives with the homoadamantane skeleton with potential antiviral activity for

• was conducted to investigate the availability of different C–H bonds in the homoadamantane skeleton for the homolytic activation, that is, abstraction by the phthalimide. The research was, furthermore, sparked by the discovery that numerous poly-azaheterocyclic adamantane derivatives show antiviral

Cross-metathesis of allylcarboranes with O-allylcyclodextrins

• Ivan Šnajdr,
• Zbyněk Janoušek,
• Jindřich Jindřich and
• Martin Kotora

Beilstein J. Org. Chem. 2010, 6, 1099–1105, doi:10.3762/bjoc.6.126

• the best of our knowledge, described. Since carboranes are of potential interest for various applications in medicine (e.g. boron neutron capture therapy for cancer, radionuclide diagnostics and therapy, and related fields [14][15][16][17], whilst some carboranes possess antiviral activity [18][19