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  • Title: Folate antagonists. 11. Synthesis and antimalarial effects of 6-[(aryloxy- and arylthio-)methyl]-2,4-pteridinediamines and -pteridinediamine 8-oxides.
    Author: Werbel LM, Johnson J, Elslager EF, Worth DF.
    Journal: J Med Chem; 1978 Apr; 21(4):337-9. PubMed ID: 349158.
    Abstract:
    Condensation of 3-amino-6-(bromomethyl)-2-pyrazinecarbonitrile 4-oxide with 4-chlorophenol gave 3-amino-6-[(4-chlorophenoxy)methyl]-2-pyrazinecarbonitrile 4-oxide (1), which was deoxygenated to obtain the de-N-oxide 4. Cyclization of 4 and 1 produced 6-[(4-chlorophenoxy)methyl]-2,4-pteridinediamine and the 8-oxide, respectively. 6-[(Arylthio)methyl]-2,4-pteridinediamines and their 8-oxides were produced analogously. Controlled oxidation of the former gave the anticipated sulfoxide 12 and sulfone 13. None of these compounds showed significant activity when tested against lethal Plasmodium berghei infections in mice or a select list of bacteria in vitro.
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