Linked Life Data

18428972

Source:http://linkedlifedata.com/resource/pubmed/id/18428972

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:dateCreated
2008-4-22
pubmed:abstractText
Cidofovir [(S)-1-(3-hydroxy-2-phosphonomethoxypropyl)cytosine] and (S)-HPMPA [(S)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine] are potent nucleoside phosphonate antiviral agents that are not orally bioavailable unless one or both of their negative charges are masked. This unit describes the synthesis of hexadecyloxypropyl esters of cidofovir and (S)-HPMPA. These prodrugs are readily absorbed after oral administration and are converted intracellularly to the corresponding diphosphates. The hexadecyloxypropyl esters of cidofovir and (S)-HPMPA are orally active in animal models of viral infection. Two synthetic strategies are employed. In the first, cyclic cidofovir is coupled to 3-hexadecyloxy-1-propanol using the Mitsunobu reaction (triphenylphosphine, DIAD), followed by basic hydrolysis of the cyclic ester. In the second, the lipid moiety is incorporated into a phosphonate synthon and a stepwise approach is used to assemble the (S)-HPMPA analog.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jun
pubmed:issn
1934-9289
pubmed:author
pubmed:issnType
Electronic
pubmed:volume
Chapter 15
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
Unit 15.2
pubmed:meshHeading
pubmed:year
2007
pubmed:articleTitle
Synthesis of cidofovir and (S)-HPMPA ether lipid prodrugs.
pubmed:affiliation
University of California, San Diego, La Jolla, California, USA.
pubmed:publicationType
Journal Article