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- W1995679404 abstract "The application of our cycloSaligenyl- (cycloSal) pronucleotide concept to the approved anti-HIV dideoxynucleoside 3′-azido-3′-deoxythymidine AZT (1) is reported. This pro-nucleotide concept has been designed to deliver the corresponding 3′-azido-3′-deoxythymidine monophosphate AZTMP (2) by selective chemical hydrolysis from the lipophilic precursors cycloSal-AZTMP 4a−h. All derivatives 4a−h were synthesized using differently substituted salicyl alcohols 7a−h as starting materials. In hydrolysis studies, compounds 4 decomposed selectively releasing AZTMP (2) and the salicyl alcohols 7 following the designed tandem reaction. Furthermore, due to the electronic properties introduced by substituents, the half-lives of the triesters 4 could be ajusted over a wide range. Phosphotriesters 4 exhibited considerable biological activity in HIV-1 and HIV-2 infected wild-type human T-lymphocyte (CEM/O) cells, whereas, contrary to our expectations, nearly all activity was lost in HIV-2 infected thymidine-kinase-deficient CEM cells." @default.
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- W1995679404 date "1998-05-01" @default.
- W1995679404 modified "2023-10-17" @default.
- W1995679404 title "Nucleotide Delivery fromcycloSaligenyl-3′-azido-3′-deoxythymidine Monophosphates (cycloSal-AZTMP)" @default.
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- W1995679404 doi "https://doi.org/10.1002/(sici)1099-0690(199805)1998:5<837::aid-ejoc837>3.0.co;2-7" @default.
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