What is it about?
Oxime is a good example of a group with steric rigidity and suitable stability up to acidic pH values. Based on the previous findings all over the world we proposed a new structural motif. We have synthesized a set of new antiviral acyclic nucleoside phosphonates bearing this group and tested them against several human viruses - HIV, HCV, HSV and HCMV. New improvements in the Mitsunobu procedure were introduced and the key intermediate, aminooxymethylphosphonate ester, was shown to be very potent for functionalization of carbonyl compounds.
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Why is it important?
Search for new drug candidates is important due to the increasing threats of epidemics caused by human immunodeficinecy virus, herpes and hepatitis C virus.
Perspectives
Novel procedures and synthesis improvements can help to functionalize other synthetic and natural products. For example, aminooxymehtylphosphonate, designed and obtained in high yield in our study, can serve as an easly "clickable" group for adding water solubility to any aldehyde- or ketone-containing derivatives.
Dr. Pavel N. Solyev
Engelhardt Institute of Molecular Biology RAS
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This page is a summary of: Versatile synthesis of oxime-containing acyclic nucleoside phosphonates – synthetic solutions and antiviral activity, Organic & Biomolecular Chemistry, January 2015, Royal Society of Chemistry,
DOI: 10.1039/c5ob01571e.
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