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Synthesis and Antiviral Evaluation of Novel 4′‐Hydroxymethyl Branched Thioapiosyl Nucleosides
Author(s) -
Kim Jin Woo,
Hong Joon Hee
Publication year - 2005
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200500174
Subject(s) - hydroxymethyl , thymine , chemistry , uracil , cytosine , moiety , stereochemistry , guanine , ozonolysis , cytotoxicity , chemical synthesis , combinatorial chemistry , organic chemistry , biochemistry , nucleotide , dna , gene , in vitro
In this study, we synthesized novel 4′‐hydroxymethyl branched thioapiosyl nucleosides. The thioapiosyl sugar moiety was constructed using sequential ozonolysis and reduction. The natural bases (uracil, thymine, cytosine, and adenine) were efficiently coupled using the Vorbrüggen glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against HIV‐1, HSV‐1, HSV‐2, and HCMV. Compound 19 showed moderate anti‐HIV activity (EC 50 = 19.3 μg/mL) without exhibiting any cytotoxicity up to 100 μM.