AIDS dementia: Synthesis and properties of a derivative of 3′-azido-3′-deoxythymidine (AZT) that may become 'locked' in the central nervous system

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Abstract

In an attempt to provide a derivative of 3′-azido-3′-deoxythymidine (AZT) which might be sequestered in the central nervous system and release AZT, the dihydropyridine ester 5′-(1,4-dihydro-1-methyl-3-pyridinylcarbonyl)-3′-deoxythymidine, was synthesized in a three step sequence. This material showed potent anti-HIV-1 activity in MT-4 cells most probably by hydrolysis to the parent nucleoside, AZT. This dihydropyridine derivative of AZT could be easily oxidized to a positively charged pyridinium derivative of AZT in rat brain cytosol. In turn the pyridinium form could be hydrolyzed, non-enzymatically, to AZT. © 1988.

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Torrence, P. F., Kinjo, J. ei, Lesiak, K., Balzarini, J., & De Clercq, E. (1988). AIDS dementia: Synthesis and properties of a derivative of 3′-azido-3′-deoxythymidine (AZT) that may become “locked” in the central nervous system. FEBS Letters, 234(1), 135–140. https://doi.org/10.1016/0014-5793(88)81319-X

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