Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.

@article{Wnuk1997AnticancerAA,
  title={Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues.},
  author={S. Wnuk and C. Yuan and R. Borchardt and J. Balzarini and E. De Clercq and M. Robins},
  journal={Journal of medicinal chemistry},
  year={1997},
  volume={40 11},
  pages={
          1608-18
        }
}
Selectively protected adenine nucleosides were converted into 5'-carboxaldehyde analogues by Moffatt oxidation (dimethyl sulfoxide/dicyclohexylcarbodiimide/dichloroacetic acid) or with the Dess-Martin periodinane reagent. Hydrolysis of a 5'-fluoro-5'-S-methyl-5'-thio (alpha-fluoro thioether) arabinosyl derivative also gave the 5'-carboxaldehyde. Treatment of 5'-carboxaldehydes with hydroxylamine [or O-(methyl, ethyl, and benzyl)hydroxylamine] hydrochloride gave E/Z oximes. Treatment of purified… Expand
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Treatment of 5'-S-(allyl and aryl)-5'-thioadenosine derivatives 2 with XeF 2 , or the corresponding sulfoxides 3 with DAST/SbCl 3 , gave diastereomeric 5'-fluoro compounds which were deprotected toExpand
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TLDR
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TLDR
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