Nucleotides. Part XXXV. Synthesis of 3′‐deoxyadenylyl‐(2′–5′)‐3′‐deoxyadenyIyl‐(2′–ω)‐9‐(ω‐hydroxyalkyl)adenines

Abstract

Via the phosphotriester approach, new structural analogs of (2′–5′)oligoadenyiates, namely 3′‐deoxyadenylyl‐(2′–5′)‐3′‐dcoxyadenylyl‐(2′–ω)‐9‐(ω‐hydroxyalkyl)adenines 18–21, have been synthesized (see Scheme) which should preserve biological activity and show higher stability towards phosphodiesterases. The newly synthesized oligonucleotides 18–21 have been characterized by 1H‐NMR spectra, TLC, and HPLC analysis.

Nucleotides. Part XLIV. Synthesis, characterization, and biological activity of monomeric and trimeric cordycepin‐cholesterol conjugates and inhibition of HIV‐1 replication

“…layer dried (MgSO,) and evaporated, and the residue purified by FC (silica gel, 14 x 3 cm, toluene+toluene/AcOEt 3:2+1:1 + 5% MeOH): 886 mg (97%) of 6. (7). To 6 (183 mg, 0.2 mmol), which was co-evaporated twice in abs.…”

“…In a one-pot reaction, 5 was obtained in 77% yield by treatment of 1 first with succinic anhydride and DMAP in CH,Cl, and secondly with cholesterol in the presence of N- [3-(dimethylamino) (EDC). Detritylation to 6 proceeded almost quantitatively and subsequent elimination of the npeoc group resulted in 57 % yield of 2'-O- [2-(cholesteryloxycar-boxyl)propionyl]-3'-deoxyadenosine (7). The relatively low yields of monomeric cordycepin conjugates 4 and 7 are due to their unusual physical properties derived from the combination of the hydrophobic cholesterol and the hydrophilic cordycepin moieties.…”