Convenient synthesis of 10-deazaaminopterin via a pteridine ylide.
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Piper JR, Montgomery JA
Convenient synthesis of 10-deazaaminopterin via a pteridine ylide.
J Med Chem. 1980 Mar;23(3):320-1.
- PubMed ID
- 7365749 [ View in PubMed]
- Abstract
10-Deazaaminopterin, a potential antitumor agent now undergoing clinical trials, has been synthesized by a new approach involving the Wittig reaction. The ylide obtained by reaction of 6-(bromomethyl)-2,4-pteridinediamine with triphenylphosphine in Me2NAc, followed by treatment with NaOMe, underwent smooth reaction with diethyl N-(4-formylbenzoyl)-L-glutamate to give the vinyl precursor of the subject compound. Catalytic hydrogenation (Pt in glacial AcOH) of this product at ambient conditions led to uptake of 3 molar equiv of H2. Exposure to air during saponification of the ester groupings apparently gave the 7,8-dihydro compound according to UV spectral data, and further oxidation with H2O2 led to 10-deazaaminopterin.
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- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Methotrexate Dihydrofolate reductase IC 50 (nM) 26 N/A N/A Details