Synthesis and antiviral evaluation of novel 3'- and 4'-doubly branched carbocyclic nucleosides as potential antiviral agents.
A series of 3'- and 4'-branched carbocyclic nucleosides 25, 26, 27, 28, 29 and 30 were synthesized starting from simple acyclic ketone derivatives. The construction of the required quaternary carbon was made using a [3,3]-sigmatropic rearrangement. In addition, the installation of a methyl group in the 3'-position was accomplished using a Horner-Wadsworth-Emmons (HWE) reaction with triethyl 2-phosphonopropionate. Bis-vinyl was successfully cyclized using a Grubbs' catalyst (II). Natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst.
Hong
Joon Hee
JH
College of Pharmacy, Chosun University, Kwangju 501-759, Korea. hongjh@chosun.ac.kr
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004686:Encephalomyocarditis virus / Q000187:drug effects / Q000254:growth & development; D015497:HIV-1 / Q000187:drug effects / Q000254:growth & development; D018259:Herpesvirus 1, Human / Q000187:drug effects / Q000254:growth & development; D018258:Herpesvirus 2, Human / Q000187:drug effects / Q000254:growth & development; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D006571:Heterocyclic Compounds; D009705:Nucleosides