Edoxudine

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Edoxudine
Edoxudin.svg
Systematic (IUPAC) name
5-ethyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Identifiers
CAS Number 15176-29-1 YesY
ATC code D06BB09 (WHO)
PubChem CID 66377
ChemSpider 59752 N
UNII 15ZQM81Y3R YesY
ChEMBL CHEMBL318153 N
Chemical data
Formula C11H16N2O5
Molar mass 256.25514
 NYesY (what is this?)  (verify)

Edoxudine (or edoxudin) is an antiviral drug. It is an analog of thymidine, a nucleoside.

It has shown effectiveness against herpes simplex virus.[1]

Synthesis[edit]

Edoxudine synthesis:[2] Synthesis via organopalladium intermediates:[3][4]

Mercuration of the 2'-deoxyuridine 1 leads to the organometallic derivative 2; reaction of that with ethylene in the presence dilithiopalladium tetrachloride gives the alkylation product 3; this is reduced catalytically in situ. There is thus obtained the antiviral agent edoxudine 4.

References[edit]

  1. ^ "Topical antiviral agents for herpes simplex virus infections". Drugs Today. 34 (12): 1013–25. December 1998. doi:10.1358/dot.1998.34.12.487486. PMID 14743269. 
  2. ^ K. K. Gauri, GB 1170565; eidem, U.S. Patent 3,553,192 (1968, 1971 both to Robugen).
  3. ^ Bergstrom, Donald E.; Ruth, Jerry L. (1976). "Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates". Journal of the American Chemical Society. 98 (6): 1587–9. doi:10.1021/ja00422a056. PMID 1249369. 
  4. ^ Bergstrom, Donald E.; Ogawa, Mark K. (1978). "C-5 substituted pyrimidine nucleosides. 2. Synthesis via olefin coupling to organopalladium intermediates derived from uridine and 2'-deoxyuridine". Journal of the American Chemical Society. 100 (26): 8106–8112. doi:10.1021/ja00494a014. ISSN 0002-7863.