Abstract
An improved synthesis of MDL 73811 - a potent AdoMetDC (S-adenosylmethionine decarboxylase) inhibitor and anti-trypanosomal compound with in vivo activity - has been completed in four steps from commercially available 2′,3′-O-isopropylideneadenosine. Utilization of Mitsunobu chemistry was crucial for the reliable and scalable introduction of the 5′-methylamine moiety, which was problematic using traditional activation/displacement chemistry as previously reported. All reactions in this synthesis were run on gram-scale resulting in a five-fold increase in yield over the original synthesis.
Original language | English (US) |
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Article number | ss-2016-m0105-op |
Pages (from-to) | 2065-2068 |
Number of pages | 4 |
Journal | Synthesis (Germany) |
Volume | 48 |
Issue number | 13 |
DOIs | |
State | Published - Jul 1 2016 |
Keywords
- Mitsunobu reaction
- drug discovery
- inhibitors
- medicinal chemistry
- nucleosides
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry