Synthesis and antiviral activities of 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-beta-D-ertythro-pentofuranosyl)uracils.
Various 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-beta-D-erythro-pentofuranosyl)uracils (4'-thioDMDUs) were synthesized from D-glucose via sila-Pummerer-type glycosylation. All of the beta-anomers of 5-substituted 4'-thioDMDU, except the 5-hydroxyethyl derivative, showed potent anti-HSV-1 activity (ED50 = 0.016-0.096 microgram/mL). 5-Ethyl- and 5-iodo-4'-thioDMDUs were also active against HSV-2 (ED50 = 0.17 and 0.86 microgram/mL, respectively). 5-Bromovinyl-4'-thioDMDU was particularly active against VZV (ED50 = 0.013 microgram/mL).
Satoh
H
H
Biochemicals Division, Yamasa Corporation, Chiba, Japan.
Yoshimura
Y
Y
Watanabe
M
M
Ashida
N
N
Ijichi
K
K
Sakata
S
S
Machida
H
H
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis*; D003841:Deoxycytidine / Q000031:analogs & derivatives / Q000494:pharmacology; D006031:Glycosylation; D006561:Herpes Simplex / Q000821:virology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010429:Pentoses / Q000138:chemical synthesis; D011743:Pyrimidines / Q000138:chemical synthesis / Q000633:toxicity; D014498:Uracil / Q000031:analogs & derivatives*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D010429:Pentoses; D011743:Pyrimidines; D003841:Deoxycytidine; D014498:Uracil; C056034:2'-deoxy-2'-methylenecytidine