Racemic synthesis and antiviral evaluation of 4'(alpha)-hydroxymethyl and 6'(alpha)-methyl substituted apiosyl nucleosides.
This article reports the novel synthesis of substituted apiosyl nucleosides. The key apiosyl intermediate 9 was constructed by sequential ozonolysis, reductions, and acetylation from the ester derivative 6. The nucleosides of uracil, thymine, cytosine, and adenine were synthesized using the glycosyl condensation procedure (silyated base and TMSOTf). The antiviral activities of the synthesized compounds against the HIV-1, HSV-1, HSV-2, and HCMV viruses were evaluated. The adenine derivative 26 showed weak anti-HIV activity (EC(50) = 10.1 microg/ml) without exhibiting any cytotoxicity up to a concentration of 100 microM.
Kim
Aihong
A
College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D000998:Antiviral Agents / Q000494:pharmacology*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D004098:Dihydroxyacetone / Q000031:analogs & derivatives / Q000138:chemical synthesis; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D010126:Ozone
D000998:Antiviral Agents; D009705:Nucleosides; D010126:Ozone; D004098:Dihydroxyacetone