Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction
of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2
t
Bu) leads to
the anti-oxyaminated product in up to 99% yield.
Use of O-methyl-N-tosyl carbamate
(R3 = CO2Me) as the nitrogen nucleophile followed
by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent
with the observed selectivities are proposed.
The neglected tropical disease leishmaniasis, caused by Leishmania spp., is becoming more problematic due to the emergence of drug-resistant strains. Therefore, new drugs to treat leishmaniasis, with novel mechanisms of action, are urgently required. Strathclyde minor groove binders (S-MGBs) are an emerging class of anti-infective agent that have been shown to have potent activity against various bacteria, viruses, fungi and parasites. Herein, it is shown that S-MGBs have potent activity against L. donovani, and that an N-oxide derivation of the tertiary amine tail of typical S-MGBs leads to selective anti-leishmanial activity. Additionally, using S-MGB-219, the N-oxide derivation is shown to retain strong binding to DNA as a 2:1 dimer. These findings support the further study of anti-leishmanial S-MGBs as novel therapeutics.
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