3,5‐Di‐( tert ‐Butyl)‐6‐fluoro‐ cyclo Sal‐d4TMP − A Pronucleotide with a Considerably Improved Masking Group | Zendy

Ducho Christian | Zendy; Wendicke Silke | Zendy; Görbig Ulf | Zendy; Balzarini Jan | Zendy; Meier Chris | Zendy

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

Author(s) -

Ducho Christian,

Wendicke Silke,

Görbig Ulf,

Balzarini Jan,

Meier Chris

Publication year - 2003

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300537

Subject(s) - chemistry , masking (illustration) , stereochemistry , butyrylcholinesterase , group (periodic table) , medicinal chemistry , organic chemistry , enzyme , aché , art , acetylcholinesterase , visual arts

A new, considerably improved cyclo Sal 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‐ cyclo Sal‐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)

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