3,5-Di-(tert-Butyl)-6-fluoro-cycloSal-d4TMP − A Pronucleotide with a Considerably Improved Masking Group

3,5-Di-(tert-Butyl)-6-fluoro-cycloSal-d4TMP − A Pronucleotide with a Considerably Improved Masking Group

A new, considerably improved cycloSal masking group has been developed. This new group combines four desirable properties and has been attached to the anti‐HIV drug 2′,3′‐dideoxy‐2′,3′‐didehydrothymidine (d4T, 1) to give 3,5‐(di‐tert‐butyl)‐6‐fluoro‐cycloSal‐d4TMP (2i). This phosphate triester has a...

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Veröffentlicht in:European journal of organic chemistry 2003-12, Vol.2003 (24), p.4786-4791
Hauptverfasser: Ducho, Christian, Wendicke, Silke, Görbig, Ulf, Balzarini, Jan, Meier, Chris
Format: Artikel
Sprache:eng
Schlagworte:
Antiviral agents
DNA
Nucleosides
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Zusammenfassung:A new, considerably improved cycloSal masking group has been developed. This new group combines four desirable properties and has been attached to the anti‐HIV drug 2′,3′‐dideoxy‐2′,3′‐didehydrothymidine (d4T, 1) to give 3,5‐(di‐tert‐butyl)‐6‐fluoro‐cycloSal‐d4TMP (2i). This phosphate triester has a reasonable chemical half‐life, highly selectively released d4TMP, has poor − if any − inhibitory effect on butyrylcholinesterase (BChE), and achieved the TK‐bypass. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300537